4-Iodo-N,N-dimethylaniline

General procedure: To a stirred solution of the substrate (1 mmol) in CHGeneral procedure: General procedure for the iodination of aryl amines under solvent-free conditions.DBDABCODCI (0.5 mmol) and aryl amine (1 mmol) were triturated together in a porcelainmortar at room temperature. After completing reaction which monitored by TLC, the ethylacetate added to mixture and filtered, the organic layer washed with 5percent aqueous sodiumthiosulfate, and dried over MgSO4. The solvent was removed in vacuum and the crude mixturewas purified by column chromatography using ethyl acetate and hexane mixture and analyzedby m.p. and 1H NMR spectroscopy.N, N-Dimethylaniline (0.1 g, 0.825 mmol) and l-butyl-3-methylpyridinium dichloroiodate (BMPDCI) (0.345 g, 0.99 mmol) were added in 10 ml one necked round bottomed flask in an inert atmosphere. The reaction mixture was heated at 80 °C for 1 hr. The reaction was monitored by TLC. After the reaction was completed (TLC), ethyl acetate (10ml) was added followed by addition of water (10ml). The entire reaction mixture was extracted with ethyl acetate (3x10ml). The combined ethyl acetate layer was washed with water, brine and dried over anhydrous sodium sulphate. The separated combined organic layers, was evaporated under vacuum, to afford the crude product. This crude product was purified by silica gel column chromatography to afford pure 4-iodo-N, N-dimethylaniline in 0.175 g, (86percent, yield). 1H NMR (CDClGeneral procedure: To a clean 50 mL round bottomed flask equipped with a large stir bar was added the substrate (10 mmol) followed by cyclohexane (ca. 6.0 mL to maintain the reaction concentration of 1.67 M) and an aqueous saturated solution of sodium carbonate (2.8 mL). Finally, iodine beads (11 mmol) were added as a solid and the flask was sealed with a septum and vented with a needle to the open atmosphere. The reaction was allowed to stir for the specified time at room temperature unless otherwise noted (see refPreviewPlaceHolderTable 1). The reaction mixture was poured into a separatory funnel with the aid of ethyl acetate or MTBE (2-3 mL) with additional aqueous saturated sodium carbonate (1 mL). The organic layer was washed twice with an aqueous saturated solution of sodium bisulfite (4 mL) and brine (5 mL), dried over sodium sulfate, and concentrated in vacuo to provide crude iodinated product. The products were purified by crystallization (if crystalline) from hexanes. Column chromatography (ethyl acetate/hexanes) was performed on the oils.4-Iodobenzenamine (1327 mg, 6.06 mmol), NaHCO3 (1140 mg, 13.57 mmol), and DMF (4 mL) were added into the 25 mL flask, the resulting mixture was stirred at rt, iodomethane (2415 mg, 17.00 mmol) was added dropwise via a dropping funnel. After the complete conversion of the starting material as monitored by TLC (eluent: petroleum ether/ethyl acetate = 2/1), the mixture was poured into cold water (10 mL), the organic layer was separated, the aqueous phase was extracted with ethyl acetate (10 mL × 3), the organic phase was combined and washed with a saturated aqueous solution of NaCl, and dried over anhydrous MgSO4. The solvent was evaporated. Flash chromatography on silica gel (eluent: petroleum ether/ethyl acetate = 10/1) afforded 4-iodo-N, N-dimethylbenzenamine as a pale yellow solid (508 mg, 34percent).General procedure: An aromaticamine (1 mmol), nanomagnetic-supported sulfonic acid (c-Fe2O3–SO3H)(0.65 g), NaNO2 (2 mmol, 0.138 g), and 0.2 mL of H2O were homogenized bygrinding in a mortar with a pestle for a few minutes. Formation of a reddishbrowngas was observed as soon as H2O was added. The diazotization reactionlasted for approximately 5–30 min. Next, KI (2.5 mmol, 0.415 g) was added tothe diazonium salt and grinding was continued for 10–20 min. After completionof the reaction, the mixture was triturated with EtOAc (5 mL). The c-Fe2O3–SO3K was separated from the solution using a magnetic bar. The organic layerwas treated with aq 10percent Na2SO3 (15 mL), then dried over anhydrous Na2SO4.After evaporation of the solvent, the crude product was afforded. Purifiedproducts were obtained by recrystallization from ethanol or by flashchromatography (n-hexane–EtOAc, 95:5).General procedure: A mixture of the arylboronic acid (0.55mmol), KF (96mg, 1.65mmol) and I4-Iodobenzenamine (1327 mg, 6.06 mmol), NaHCO3 (1140 mg, 13.57 mmol), and DMF (4 mL) were added into the 25 mL flask, the resulting mixture was stirred at rt, iodomethane (2415 mg, 17.00 mmol) was added dropwise via a dropping funnel. After the complete conversion of the starting material as monitored by TLC (eluent: petroleum ether/ethyl acetate = 2/1), the mixture was poured into cold water (10 mL), the organic layer was separated, the aqueous phase was extracted with ethyl acetate (10 mL × 3), the organic phase was combined and washed with a saturated aqueous solution of NaCl, and dried over anhydrous MgSO4. The solvent was evaporated. Flash chromatography on silica gel (eluent: petroleum ether/ethyl acetate = 10/1) afforded 4-iodo-N, N-dimethylbenzenamine as a pale yellow solid (508 mg, 34%).General procedure: To a solution of aniline (1 mmol) in glacial acetic acid (7 mL) under argon was added paraformaldehyde (10 mmol) and sodium cyanoborohydride (5 mmol). After stirring overnight, the reaction mixture was poured into ice cooled water (?100 mL) containing NaOH (7 g). This mixture (pH 14) was extracted thrice with CH2Cl2 (3 × 350 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to obtain the crude product. Flash chromatographic purification of the crude product using silica gel and a mixture of hexane and ethyl acetate as the eluent provided the pure product.General procedure: 4-Ethyl aniline (8.252 mmol) was dissolved in 50 mL of glacial acetic acid under inert N2 condition. Paraformaldehyde (80.871 mmol) was added and the contents were stirred for 15 min. Sodium cyanoborohydride (38.785 mmol) was added as the next step and it was stirred overnight at room temperature. The reaction mixture was poured in the saturated Sodium hydroxide solution, which contained crushed ice. Ethyl acetate was added later and the upper layer was collected which contained the compound and was further subjected to solvent evaporation.

Molecular Weight:247.08
XLogP3:3.1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:246.98580
Monoisotopic Mass:246.98580
Topological Polar Surface Area:3.2
Heavy Atom Count:10
Complexity:95.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes