Water → 5-Thiazolecarboxylic acid, 2-(3-cyano-4-(2-methylpropoxy)phenyl)-4-methyl-, ethyl ester

HRID 1406841Notes

Reaction equation

HRID 1406841 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[CH:8]([CH3:10])[CH3:9].[CH2:12]([O:14][C:15]([C:17]1[S:21][C:20]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([C:29]#[N:30])[CH:23]=2)=[N:19][C:18]=1[CH3:31])=[O:16])[CH3:13].O>CN(C)C=O>[CH2:12]([O:14][C:15]([C:17]1[S:21][C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:7][CH:8]([CH3:10])[CH3:9])=[C:24]([C:29]#[N:30])[CH:23]=2)=[N:19][C:18]=1[CH3:31])=[O:16])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 135627703Ethyl 2-(3-Cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 98845495-Thiazolecarboxylic acid, 2-(3-cyano-4-(2-methylpropoxy)phenyl)-4-methyl-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Potassium carbonate (300 g, 2.17 mol) and isobutyl bromide (142.7 g, 1.041 mol) were added to a solution of ethyl-2-(3-cyano-4-hydroxyphenyl)-4-methyl-5-thiazole carboxylate (100 g, 0.347 mol) in dimethylformamide (300 mL), and the reaction mixture was heated at a temperature of about 75° C. for about 8 hours. After completion of reaction, the reaction mixture was cooled to about 40° C. and water was added. The reaction mixture was further cooled to about 0° C. and stirred for about 1 hour. The solid thus obtained was filtered, washed with water and dried to give title compound. (Yield: 111g, 92.9%)

Workup

  1. customAfter completion of reaction
  2. temperaturethe reaction mixture was cooled to about 40° C.
  3. temperatureThe reaction mixture was further cooled to about 0° C.
  4. customThe solid thus obtained
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-3769dc26d12c48e88bf5b45047143597
Source dataset
uspto-grants-2014_12
Patent number
US08916713B2

Reaction notes

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