Potassium Carbonate → Ethyl 2-amino-5-(2,6-difluorophenyl)-1,3-thiazole-4-carboxylate

HRID 383929Notes

Reaction equation

HRID 383929 reaction equation
Cl[C:2]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]([C:5]2[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=2[F:12])O1.[NH2:18][C:19]([NH2:21])=[S:20].C([O-])([O-])=O.[K+].[K+]>CCO>[NH2:21][C:19]1[S:20][C:4]([C:5]2[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=2[F:12])=[C:2]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2723790ThioureaHCID 59291325Ethyl 2-chloro-3-(2,6-difluorophenyl)oxirane-2-carboxylate

Product 1

HCID 59291235Ethyl 2-amino-5-(2,6-difluorophenyl)-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-chloro-3-(2,6-difluorophenyl)oxirane-2-carboxylate in EtOH was added thiourea, followed by heating under reflux for 4 hours. To the reaction mixture was added ice-water, followed by addition of K2CO3 to make it basic. The solid precipitated was collected by filtration and washed with water to obtain ethyl 2-amino-5-(2,6-difluorophenyl)-1,3-thiazole-4-carboxylate as a yellow solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. customThe solid precipitated
  4. filtrationwas collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-5f2f6b8655a94845b138df85f12f19f3
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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