Thiourea → Ethyl 2-amino-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboxylate

HRID 1530126Notes

Reaction equation

HRID 1530126 reaction equation
Br[CH:2]([C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:18][C:19]([NH2:21])=[S:20]>C(O)C>[NH2:21][C:19]1[S:20][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[N:18]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58094874Ethyl 2-bromo-3-(2,4-dichlorophenyl)-3-oxopropanoate

Product 1

HCID 58094863Ethyl 2-amino-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-bromo-3-(2,4-dichlorophenyl)-3-oxopropanoate (5.14 g, 15.1 mmol) in ethanol (90 mL) was added thiourea (1.26 g, 16.6 mmol) and the solution was stirred at reflux for 2 hours. The reaction was allowed to cool to room temperature, then the solvent was evaporated in vacuo. Column chromatography was performed to yield the title compound (4.79 g, 99%). LCMS: (AA) ES+, 319. 1H NMR (300 MHz, d1-chloroform) δ: 8.11 (br s, 2H), 7.52-7.33 (m, 3H), 4.24-4.16 (m, 2H), 1.23-1.17 (m, 3H).

Workup

  1. temperatureat reflux for 2 hours
  2. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-52e14a88c4824eb98d8b02fdf1f29501
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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