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2-amino-N-(2-methylphenyl)-5-thiazolecarboxamide synthesis
- Product Name:2-amino-N-(2-methylphenyl)-5-thiazolecarboxamide
- CAS Number:1184914-03-1
- Molecular formula:C11H11N3OS
- Molecular Weight:233.29
Yield:1184914-03-1 63.5%
Reaction Conditions:
Stage #1: (E)-N-(2-methylphenyl)-3-ethoxyacrylamidewith N-Bromosuccinimide in 1,4-dioxane;water at 0 - 20; for 3 h;
Stage #2: thiourea in 1,4-dioxane;water at 70; for 2 h;
Steps:
2-Amino-N-arylthiazole-5-carboxamides 5a-5c
General procedure: To a solution of 3a-3c (25 mmol) in 40 cm3 H2O and40 cm3 1,4-dioxane was added 4.4 g NBS (25 mmol) at0 C, while kept stirring for 1 h, after warmed to roomtemperature and stirred for another 2 h, 4.4 g thiourea(25 mmol) was added, the mixture was allowed to 70 Cand stirred for 2 h, the pH of the resultant was adjusted to8-9 by ammonia and then concentrated in vacuo. Thecrude product was crystallized from toluene, affording thecounterparts 5a-5c.
References:
Zhou, Ying;He, XiaoBing;Xiong, YuanZhen;Chai, XingXing;Chen, HongPing [Monatshefte fur Chemie,2015,vol. 146,# 6,art. no. 1403,p. 997 - 1003]
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