Water → Ethyl 2-amino-4-(4-fluorophenyl)-1,3-thiazole-5-carboxylate

HRID 1660562Notes

Reaction equation

HRID 1660562 reaction equation
Cl[C:2]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=O.[NH2:17][C:18]([NH2:20])=[S:19].O>C(O)C>[NH2:20][C:18]1[S:19][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:4]([C:3]2[CH:12]=[CH:13][C:14]([F:16])=[CH:15][CH:2]=2)[N:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2723790ThioureaHCID 54191286Ethyl 3-(2-chloro-4-fluorophenyl)-3-oxopropanoate

Product 1

HCID 12801683Ethyl 2-amino-4-(4-fluorophenyl)-1,3-thiazole-5-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10.5 g (0.05 mole) of ethyl p-fluorobenzoylacetate, 6.7 g (0.05 mole) of sulfuryl chloride and 30 ml. of chloroform was held at reflux for 18 hours and cooled. The chloroform solution was washed with water, dried (MgSO4) and concentrated under reduced pressure. The residue was distilled to give 10.8 g (88%) of ethyl 2-chloro-(p-fluoro)-benzoylacetate as an oil. A mixture of 10.8 g (0.441 mole) of ethyl 2-chloro-(p-fluoro)-benzoylacetate, 3.36 g (0.0441 mole) of thiourea, 20 ml. of water and 10 ml. of ethanol was held at reflux for 3 hours. Ethanol was removed under reduced pressure. The residue was made basic with saturated sodium bicarbonate. The solid was filtered, washed with water and recrystallized from ethanol to give 8.9 g (76%) of ethyl 2-amino-4-(p-fluorophenyl)-5-thiazolecarboxylate as white prisms, m.p. 205°-208° C.

Workup

  1. temperatureat reflux for 3 hours
  2. customEthanol was removed under reduced pressure
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-96e8b97765cd4c2294e0a0ae8bcaa783
Source dataset
uspto-grants-1981_12
Patent number
US04308391

Reaction notes

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