Potassium Hydroxide → HCID 86599619, compound

HRID 2222208Notes

Reaction equation

HRID 2222208 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([O:19][CH3:20])[CH:13]=2)[S:8][C:9]=1[CH3:10])=[O:4].[OH-].[K+].[K]>C1COCC1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:7]2[S:8][C:9]([CH3:10])=[C:5]([C:3]([OH:4])=[O:2])[N:6]=2)=[CH:13][C:14]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 5462222PotassiumHCID 86599618HCID 86599618, compound

Product 1

HCID 86599619HCID 86599619, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 6.0 g (19 mmol) 2-(4-chloro-3-methoxy-phenylamino)-5-methyl-thiazole-4-carboxylic acid methyl ester and 11.5 mL 5M aq. KOH in 60 mL THF was heated to 50° C. for 3 h. Upon cooling to room temperature the potassium salt of the product precipitated and was filtered off. This solid was dissolved in a mixture of water (250 mL) and acetic acid (12 mL) and the solution was extracted thrice with ethyl acetate. Organic phases were pooled washed with water and the solvent was removed. The residue was stirred with dichloromethane/n-heptane (1: 1; 30 mL) and the solid was isolated by filtration. Residual solvent was removed in vacuo to yield 4.4 g (77%) of the title compound.

Workup

  1. customprecipitated
  2. filtrationwas filtered off
  3. dissolutionThis solid was dissolved in a mixture of water (250 mL) and acetic acid (12 mL)
  4. extractionthe solution was extracted thrice with ethyl acetate
  5. washOrganic phases were pooled washed with water
  6. customthe solvent was removed
  7. customthe solid was isolated by filtration
  8. customResidual solvent was removed in vacuo

Sources & evidence

ORD record
ord-ba9f455f396943a78d1f38d151a4ec67
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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