Potassium Carbonate → HCID 69290180, compound

HRID 2222206Notes

Reaction equation

HRID 2222206 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[N:13]=2)=[CH:4][C:3]=1[O:17][CH3:18].[Cl:19][C:20]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Cl:19][C:20]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:21]=1[C:22]([N:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:17][CH3:18])[CH:4]=1)[C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[N:13]=1)=[O:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 666452,4-Dichlorobenzoyl chlorideHCID 86056614HCID 86056614, compound

Product 1

HCID 69290180HCID 69290180, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5.0 g (17 mmol) 2-(4-chloro-3-methoxy-phenylamino)-thiazole-4-carboxylic acid, 9.2 g (44 mmol) 2,4-dichloro-benzoyl chloride and 2.45 g (17.7 mmol) potassium carbonate in 250 mL THF was stirred at 50° C. for 18 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 5.8 g (72%) 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-84c975c07a7e4f92a5a1922d479cf17e
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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