5-Thiazolecarboxylic acid, 2-[3-formyl-4-(2-methylpropoxy)phenyl]-4-methyl-, ethyl ester
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![5-Thiazolecarboxylic acid, 2-[3-formyl-4-(2-methylpropoxy)phenyl]-4-methyl-, ethyl ester structure](https://file.echemi.com/fileManage/upload/canonicalSmiles/20220812/61261491b0e04c56814cb85390314451.png "5-Thiazolecarboxylic acid, 2-[3-formyl-4-(2-methylpropoxy)phenyl]-4-methyl-, ethyl ester")
5-Thiazolecarboxylic acid, 2-[3-formyl-4-(2-methylpropoxy)phenyl]-4-methyl-, ethyl ester
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CAS No:
161798-03-4
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Formula:
C18H21NO4S
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Chemical Name:
5-Thiazolecarboxylic acid, 2-[3-formyl-4-(2-methylpropoxy)phenyl]-4-methyl-, ethyl ester
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Synonyms:
5-Thiazolecarboxylic acid,2-[3-formyl-4-(2-methylpropoxy)phenyl]-4-methyl-,ethyl ester;Ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate;Ethyl 2-[3-formyl-4-(2-methylpropoxy)phenyl]-4-methyl-5-thiazolecarboxylate
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CAS No:
5-Thiazolecarboxylic acid, 2-[3-formyl-4-(2-methylpropoxy)phenyl]-4-methyl-, ethyl ester Basic Attributes
347.43
347.43
700-743-7
DTXSID90447849
2934100090
Safety Information
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|Aggregated GHS information provided by 3 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
5-Thiazolecarboxylic acid, 2-[3-formyl-4-(2-methylpropoxy)phenyl]-4-methyl-, ethyl ester Use and Manufacturing
Preparation of Compound of formula III)[0094] A compound of formula II (10.0 gr, 34.33 mmol) was reacted with iso- butyl bromide (18.9 gr, 137.3 mmol) in the presence of potassium carbonate (19.0 gr, 137.3 mmol) and potassium iodide (2.3 gr, 13.7 mmol) in 60 ml dimethylformamide. The reaction was performed at about 70°C during 4 hours. The reaction mixture was extracted at 70°C using 300 ml ethyl acetate and 600 ml water. The separated aqueous phase was washed twice with 100 ml ethyl acetate. The combined organic phase was washed twice with 100 ml water and then concentrated to dryness. The resulting solid residue was re- crystallized from 70 ml ethyl acetate, filtered and dried under reduced pressure at about 40°C to provide a compound of formula III (8.9 gr, yield - 83percent). The Compound of formula III purity is 99.1percent (by HPLC).Dissolve 14.14g of ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate (Formula III) in 55 ml dimethylformamide, at ambient temperature. Add 40g of potassium carbonate, along with 15.9 ml isobutyl bromide. Heat the reaction to 75-80 °C and stir for 4 hours. Cool to 25-30 °C, while 165 ml process water is added. Further cool to 0-5 °C and stir for 30 minutes at this temperature. Filter off the precipitated solid and wash the filter cake with 55 ml process water. The wet cake is dried under vacuum at 40 °C for 7 hours, to furnish 16.43 g of ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate (Formula lib). of compound of formula IllbFormylation reaction is complete, no need to separate, Continue the next isobutylation reaction, DMF as the reaction solvent, 164g of dimethylformamide was added, dissolved, Then add 14g potassium carbonate, 21.7g bromoisobutane was added dropwise, the reaction was warmed, The reaction temperature is controlled at 60-115 ° C, The reaction time is 3-10 hours, the reaction was completely detected by HPLC, Slowly dropping 76g of water, Cooled to room temperature filtered, centrifuged, Centrifuge the filter cake first with 50g DMF (dimethylformamide) once, high-speed spin-dry;Then washed with 19g of water for the first time, High-speed centrifuge drying, washing with 19g water a second time, High-speed centrifuge drying;Finally, the first wash with 15g methanol, High-speed centrifuge drying, washed with 15g methanol second time, High-speed centrifuge drying;The wet product was dried to give 34.2 g of ethyl 2- (3-aldehyde-4-isobutyloxyphenyl) -4-methylthiazole-5-Chromatographic purity of 99.2percentContent of 99.5percent, two-step total yield of 68.2percent.4. lg of the compound having the formula (VI) dissolved in structure 80mLDMF added ethyl-chloroacetoacetate 3. 89g, 60 ° C for 4 hours, the reaction was stopped by filtration to obtain a solid reaction mixture was cooled, ethyl acetate 4. 5g recrystallized white solid 2- (3-aldehyde-4-isobutyloxyphenyl) -4-methyl-thiazole-5-carboxylate, namely the compound having the formula (VII) structure, to close It was 97percent.4. lg of the compound having the formula (VI) dissolved in structure 80mLDMF added ethyl-chloroacetoacetate 3. 89g, 60 ° C for 4 hours, the reaction was stopped by filtration to obtain a solid reaction mixture was cooled, ethyl acetate 4. 5g recrystallized white solid 2- (3-aldehyde-4-isobutyloxyphenyl) -4-methyl-thiazole-5-carboxylate, namely the compound having the formula (VII) structure, to close It was 97percent.
Computed Properties
Molecular Weight:347.4
XLogP3:4.3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:8
Exact Mass:347.11912932
Monoisotopic Mass:347.11912932
Topological Polar Surface Area:93.7
Heavy Atom Count:24
Complexity:431
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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