Potassium Carbonate → HCID 69286941, compound

HRID 2222209Notes

Reaction equation

HRID 2222209 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][C:11]([CH3:17])=[C:12]([C:14]([OH:16])=[O:15])[N:13]=2)=[CH:4][C:3]=1[O:18][CH3:19].[Cl:20][C:21]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Cl:20][C:21]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:22]=1[C:23]([N:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:18][CH3:19])[CH:4]=1)[C:9]1[S:10][C:11]([CH3:17])=[C:12]([C:14]([OH:16])=[O:15])[N:13]=1)=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 666452,4-Dichlorobenzoyl chlorideHCID 86599619HCID 86599619, compound

Product 1

HCID 69286941HCID 69286941, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4.3 g (14 mmol) 2-(4-chloro-3-methoxy-phenylamino)-5-methyl-thiazole-4-carboxylic acid, 7.5 g (35 mmol) 2,4-dichloro-benzoyl chloride and 2.01 g (14.5 mmol) potassium carbonate in 200 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 6.6 g (97%) 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-91f84eb4d7cd4e3ba9d96c9a7880edb1
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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