Water → HCID 118555050, compound

HRID 1051302Notes

Reaction equation

HRID 1051302 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[N:8]=[C:9]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]=[C:25]([CH3:27])[CH3:26])=[C:19]([N:28]3[CH:32]=[N:31][N:30]=[N:29]3)[CH:18]=2)[S:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[OH2:33]>C(OCC)(=O)C>[OH:33][C:25]([CH3:27])([CH3:26])[CH2:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:9]2[S:10][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]([CH3:6])[N:8]=2)=[CH:18][C:19]=1[N:28]1[CH:32]=[N:31][N:30]=[N:29]1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 118555048HCID 118555048, compound

Product 1

HCID 118555050HCID 118555050, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °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. temperaturewas heated
  2. temperatureThe reaction mixture solution was cooled to room temperature
  3. stirringunder stirring
  4. concentrationthe organic phase was concentrated
  5. custompurified

Sources & evidence

ORD record
ord-e89aa268304b4369ababf878d176e036
Source dataset
uspto-grants-2016_07
Patent number
US09388174B2

Reaction notes

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