Water → HCID 118555048, compound

HRID 1051301Notes

Reaction equation

HRID 1051301 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:11]([CH3:13])[N:12]=2)=[CH:4][C:3]=1[N:19]1[CH:23]=[N:22][N:21]=[N:20]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][C:32]([CH3:34])=[CH2:33].O>CN(C)C=O.C(OCC)(=O)C>[CH3:13][C:11]1[N:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][CH:31]=[C:32]([CH3:34])[CH3:33])=[C:3]([N:19]3[CH:23]=[N:22][N:21]=[N:20]3)[CH:4]=2)[S:9][C:10]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 3577853-Bromo-2-methyl-1-propeneHCID 136969441HCID 136969441, compound

Product 1

HCID 118555048HCID 118555048, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution was prepared by dissolving 33.1 mg of ethyl 2-[4-hydroxy-3-(1H-1,2,3,4-tetrazol-1-yl)phenyl]-4-methyl-1,3-thiazole-5-carboxylate in 1.0 mL of dimethylformamide. A reaction mixture solution prepared by adding 20.7 mg of potassium carbonate and 16.2 mg of 3-bromo-2-methylpropene to the solution was heated under stirring at 100° C. for 4 hours. The reaction mixture solution was cooled to room temperature and then 3 mL of water and 4 mL of ethyl acetate were added under stirring, followed by concentrating the organic phase to obtain 34.1 mg of ethyl 4-methyl-2-{4-[(2-methylpropen-1-yl)oxy]-3-(1H-1,2,3,4-tetrazol-1-yl)phenyl}-1,3-thiazole-5-carboxylate. (2) A reaction mixture solution prepared by adding 1.0 mL of 35% sulfuric acid aqueous solution to 34.1 mg of ethyl 4-methyl-2-{4-[(2-methylpropen-1-yl)oxy]-3-(1H-1,2,3,4-tetrazol-1-yl)phenyl}-1,3-thiazole-5-carboxylate was heated under stirring at 80° C. for 4 hours. The reaction mixture solution was cooled to room temperature and then 3 mL of water and 4 mL of ethyl acetate were added under stirring, and the organic phase was concentrated and purified using a conventional method to obtain 9.9 mg of ethyl 2-[4-(2-hydroxy-2-methylpropoxy)-3-(1H-1,2,3,4-tetrazol-1-yl)phenyl]-4-methyl-1,3-thiazole-5-carboxylate.

Workup

  1. customA solution was prepared
  2. customA reaction mixture solution prepared
  3. temperaturewas heated
  4. temperatureThe reaction mixture solution was cooled to room temperature
  5. stirringunder stirring
  6. concentrationby concentrating the organic phase

Sources & evidence

ORD record
ord-79573b5a1d85458592b1e03aa0cfee64
Source dataset
uspto-grants-2016_07
Patent number
US09388174B2

Reaction notes

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