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N-Carbethoxyphthalimide

N-Carbethoxyphthalimide structure

CAS No:
22509-74-6
Formula:
C11H9NO4
Chemical Name:
N-Carbethoxyphthalimide
Synonyms:
2H-Isoindole-2-carboxylic acid,1,3-dihydro-1,3-dioxo-,ethyl ester;2-Isoindolinecarboxylic acid,1,3-dioxo-,ethyl ester;Ethyl N-phthaloylcarbamate;N-Carbethoxyphthalimide;N-(Ethoxycarbonyl)phthalimide;N-Carboethoxyphthalimide;Nefkens' reagent;2-(Carbethoxy)phthalimide;Reagents,Nefkens';Carbethoxyphthalimide;NSC 76576;Ethyl 1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate;ethyl 1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate;Ethyl 1,3-dioxo-1,3-dihydroisoindole-2-carboxylate;1,3-Dioxo-1,3-dihydroisoindole-2-carboxylic acid ethyl ester;Ethyl 1,3-dioxoisoindoline-2-carboxylate;Ethyl 1,3-dioxo-2,3-dihydro-1H-isoindole-2-carboxylate;1,3-Dioxoisoindoline-2-carboxylic acid ethyl ester;2632247-56-2
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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Description

White crystalline powder

N-Carbethoxyphthalimide Basic Attributes

Molecular Weight：

219.19

Exact Mass：

219.19

BRN：

196340

EC Number：

245-048-5

UNII：

DGO9NPX8LS

NSC Number：

76576

DSSTox ID：

DTXSID7066805

HScode：

29251995

Characteristics

PSA：

63.7

XLogP3：

1.9

Appearance：

White Crystalline Powder

Density：

1.4±0.1 g/cm3

Melting Point：

90-92 °C

Boiling Point：

360°C (rough estimate)

Flash Point：

167.8±23.2 °C

Refractive Index：

1.595

Water Solubility：

H2O: insoluble

Storage Conditions：

0-6°C

Safety Information

Hazard category：

IRRITANT

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

22-36/37/38-20/21/22

safety instructions：

22-24/25-36/37/39-26-36

RTECS Number：

NR3459500

Marks：

Precautionary statement(s)：

P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501

Hazard Statements：

H302

GHS Classification：

|Danger|H315 (97.1%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P310, P321, P332+P313, P333+P313, P362, P363, and P501|Aggregated GHS information provided by 69 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

N-Carbethoxyphthalimide Use and Manufacturing

Methods of Manufacturing

General procedure: To a solution of phthalimide (7.36 g, 50.00 mmol) dissolved inanhydrous DMF (25 mL) was added TEA (9 mL, 65.00 mmol). Thentemperature of the reaction system was cooled to 0 C and ethylchloroformate (5.7 mL, 60.00 mmol) was added dropwise. Themixture stirred at room temperature for 2 h and poured into icewater, filtered. The solid was washed with cold water and driedto obtain 8.67 g (79.1percent yield) as white solid. Mp 81.4–83.6 C. 1HNMR (CDCl3, 400 MHz) d 1.44 (s, 3H, CH3), 4.48 (q, J = 7.1 Hz, 2H, CH2), 7.80–7.85 (m, 2H, Ar-H), 7.93–7.99 (m, 2H, Ar-H). MS (ESI):m/z 220.1 [M+H]+.The phthalimide (7.36g, 50mmol) dissolved in DMF (25 ml) in, add triethylamine (9 ml, 65mmol), 0 °C dropping to the reaction system under Chlorization ethyl acetate (5.7 ml, 60mmol), slowly to the room temperature, TLC detection reaction, 2h end of the reaction, the reaction the fluid leans poured into ice water, filtered, the filter cake is washed with ice-water washing, vacuum dried to obtain the pure N-ethyl acetate phthalimide 8.67g, yield 79.1percent81 4-f ( 3-(3-chlorophen vDimidazof 1 , 2-blo yridazin-6-yl)amino)cvclohexane- 1 - sulfonamide (EX. 8-81). [00485] To a solution of isoindoline-1 , 3-dione (2 g, 13.6 mmol) in EtTo a solution of isoindoline-1, 3-dione (2 g, 13.6 mmol) in EtTo a solution of phthalimide (2 g, 13.59 mmol) and TEA (2.75 g, 27.18 mmol) in DMF (10 mL) at 0-5°C in a 100 mL round bottom flask under an argon atmosphere, was added ethyl chloro formate dropwise over a period of 30 min. After complete addition, the reaction mixture was allowed to warm to ambient temperature and further stirred for 2h. After completion of reaction (TLC was used to monitor the reaction using 30percent EtOAc in petroleum ether, UV active), the reaction mixture was treated with ice water to afford a white precipitate. The precipitate was filtered and washed with ice water to obtain ethyl 1, 3-dioxoisoindoline-2-carboxylate as a white solid. Yield 1.5g (50.34 percent). m/z (ESI): 220.2.

Manufacturing Info：

2H-Isoindole-2-carboxylic acid, 1,3-dihydro-1,3-dioxo-, ethyl ester: ACTIVE

Computed Properties

Molecular Weight:219.19
XLogP3:1.9
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:219.05315777
Monoisotopic Mass:219.05315777
Topological Polar Surface Area:63.7
Heavy Atom Count:16
Complexity:315
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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