Thiourea → 5-Thiazolecarboxylic acid, 2-amino-4-(trifluoromethyl)-, ethyl ester

HRID 1020342Notes

Reaction equation

HRID 1020342 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[F:5][C:6]([F:17])([F:16])[C:7](=O)[CH:8](Cl)[C:9]([O:11][CH2:12][CH3:13])=[O:10]>CCO>[NH2:1][C:2]1[S:3][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([C:6]([F:5])([F:17])[F:16])[N:4]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 2737165Ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate

Product 1

HCID 676565-Thiazolecarboxylic acid, 2-amino-4-(trifluoromethyl)-, ethyl esterYield 108.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of thiourea (3.3 g, 22.88 mmol) in EtOH (200 mL) was added ethyl 4,4,4-trifluoro-2-chloroacetoacetate (5 g, 22.88 mmol), and the resulting reaction mixture was heated at 80° C. for 24 h. Then, the reaction mixture was cooled to RT and concentrated in vacuo. The product was purified by column chromatography to give ethyl 2-amino-4-trifluoromethylthiazole-5-carboxylate (A-32) as a colorless oil (5.98 g, 85% yield). 1H NMR (500 MHz, CDCl3) δ 4.32 (q, 2H, J=7.0 Hz), 3.56 (m, 4H), 1.70 (m, 6H), 1.36 (t, 3H, J=7.0 Hz); LCMS (ESI) [M+1]+ 309.3.

Workup

  1. customthe resulting reaction mixture
  2. temperatureThen, the reaction mixture was cooled to RT
  3. concentrationconcentrated in vacuo
  4. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-218617cdd96144f19f45b62f713c7c65
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

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