Potassium Carbonate → HCID 69289308, compound

HRID 2222202Notes

Reaction equation

HRID 2222202 reaction equation
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[S:12][CH:13]=[C:14]([C:16]([OH:18])=[O:17])[N:15]=2)=[CH:6][CH:5]=1.[Cl:21][C:22]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Cl:21][C:22]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:23]=1[C:24]([N:10]([C:7]1[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:19])[F:20])=[CH:5][CH:6]=1)[C:11]1[S:12][CH:13]=[C:14]([C:16]([OH:18])=[O:17])[N:15]=1)=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27365462-Chloro-4-fluorobenzoyl chlorideHCID 336793012-[[4-(Trifluoromethoxy)phenyl]amino]-4-thiazolecarboxylic acid

Product 1

HCID 69289308HCID 69289308, compoundYield 111.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2.0 g (6.6 mmol) 2-(4-(trifluoromethoxy)phenylamino)-thiazole-4-carboxylic acid, 3.17 g (16.4 mmol) 2-chloro-4-fluorobenzoyl chloride and 0.92 g (6.6 mmol) potassium carbonate in 50 mL THF was stirred at 50° C. for 48 h. After evaporation of the volatiles the residue was partitioned between water and ethyl acetate. Organic phases were pooled, dried with MgSO4 and the solvent was removed in vacuo. Crystallisation from n-heptane/ethyl acetate yielded 3.4 g of the title compound which was used without further purification.

Workup

  1. customAfter evaporation of the volatiles the residue
  2. customwas partitioned between water and ethyl acetate
  3. dry with materialdried with MgSO4
  4. customthe solvent was removed in vacuo
  5. customCrystallisation from n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-3386f76894334d77a5642e016d32ca6d
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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