Dimethylformamide → 3-(2-Methyl-thiazol-4-yl)-phenylamine

HRID 255900

Reaction equation

HRID 255900 reaction equation
Br.[NH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6](=O)[CH2:7]Br.[C:13]([NH2:16])(=[S:15])[CH3:14].CN(C)C=O.[OH-].[Na+]>O>[CH3:14][C:13]1[S:15][CH:7]=[C:6]([C:5]2[CH:10]=[CH:11][CH:12]=[C:3]([NH2:2])[CH:4]=2)[N:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 2723949ThioacetamideHCID 201651043-Amino-phenacyl bromide hydrobromide

Product 1

HCID 7365353-(2-Methyl-thiazol-4-yl)-phenylamineYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-amino-phenacyl bromide hydrobromide (11.78 g), thioacetamide (3 g) and dimethylformamide (20 ml) was stirred at room temperature for 24 hours and then poured into water (100 ml). The resulting solution was made alkaline with 10% sodium hydroxide, and the precipitate was filtered off and dried to give 6 g of 2-methyl-4-(3-amino-phenyl)-thiazole; M.p. 134°-137° C.

Workup

  1. filtrationthe precipitate was filtered off
  2. customdried

Sources & evidence

ORD record
ord-6884dac1deb44f1293e4f4875b0ec887
Source dataset
uspto-grants-1987_10
Patent number
US04699915

Linked notes

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