ChemicalBook CAS DataBase List 2-(4-AMINO-PHENYL)-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER

2-(4-AMINO-PHENYL)-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER synthesis

4synthesis methods

Product Name:2-(4-AMINO-PHENYL)-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
CAS Number:730234-73-8
Molecular formula:C12H12N2O2S
Molecular Weight:248.3

78979-64-3 Synthesis

2-(4-NITRO-PHENYL)-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER

78979-64-3
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2-(4-AMINO-PHENYL)-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER

730234-73-8
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Yield:730234-73-8 66%

Reaction Conditions:

with ammonium formate;palladium 10% on activated carbon in ethanol at 20; for 36 h;

Steps:

1.c

A solution of ethyl 2- (4-nitrophenyl) thiazole-4-carboxylate (2) (3.8g, 13.7mmol) and ammonium formate (5.17g, 82mmol) in ethanol (200mL) was stirred at room temperature. To this was added a suspension of 10% w/w palladium on charcoal (1.14g, 30% w/w) in ethanol (50mL). The reaction mixture was stirred for 36 hours at room temperature then filtered through celite. The celite pad was washed with hot ethanol (2 x 50mL). The combined filterates were concentrated to give a cream coloured crystalline solid 3 (3.65g). This was washed with water (3 x 50mL) and dried under vacuum. The yield was 2.252g, 66%). 1H NMR (d6-DMSO) 5 8.32 (1H, s, H-5), 7.65 (2H, d, J = 8.6Hz, H- 2', 6'), 6.65 (2H, d, J = 8.6Hz, H-3', 5'), 5.77 (2H, bs, N-H), 4.32 (2H, t, J = 7.2Hz, CH2), 1.33 (3H, t, J = 7.2Hz, CH3) ; 13C NMR (d6- DMSO) 5 168.9, 160.9, 151.5, 146.4, 127.8 (CH), 126.4 (CH), 119.9, 113.6 (CH), 60.6 (CH2), 14.2 (CH3).

References:

WO2005/85177,2005,A2 Location in patent:Page/Page column 39-40