Potassium Carbonate → HCID 69287841, compound

HRID 2222203Notes

Reaction equation

HRID 2222203 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]([Cl: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]([Cl: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 666452,4-Dichlorobenzoyl chlorideHCID 336793012-[[4-(Trifluoromethoxy)phenyl]amino]-4-thiazolecarboxylic acid

Product 1

HCID 69287841HCID 69287841, compoundYield 79.4%

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, 3.44 g (16.4 mmol) 2,4-dichloro-benzoyl 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 2.5 g (79%) of the title compound.

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-e9bb583d58454507b8b1f3c10f527638
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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