Water → HCID 19965167, compound

HRID 977105Notes

Reaction equation

HRID 977105 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][C:11]([C:15]([O:17]CC)=[O:16])=[C:12]([CH3:14])[N:13]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[CH:27]([CH3:29])[CH3:28].O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][C:11]([C:15]([OH:17])=[O:16])=[C:12]([CH3:14])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:26][CH:27]([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 135737461HCID 135737461, compound

Product 1

HCID 19965167HCID 19965167, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

340 mg of the phenol derivative prepared in step (1) was suspended in 5 ml of N,N-dimethylformamide, 690 mg of anhydrous potassium carbonate and 690 mg of isobutyl bromide were added thereto, and the mixture was stirred at 70° C. for 24 hours. After the completion of the reaction, the reaction product was poured into water, and the mixture was extracted with ether. The organic layer was concentrated to give a crystalline product. This product was hydrolyzed by a conventional process and purified by recrystallization to give 310 mg of 2-(3-bromo-4-isobutyloxyphenyl)-4-methyl-5-thiazolecarboxylic acid (yield: 78%).

Workup

  1. customAfter the completion of the reaction
  2. extractionthe mixture was extracted with ether
  3. concentrationThe organic layer was concentrated
  4. customto give a crystalline product
  5. custompurified by recrystallization

Sources & evidence

ORD record
ord-30c4912347554dfb9c67a185b0311749
Source dataset
uspto-grants-1997_03
Patent number
US05614520

Reaction notes

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