Hydrochloric Acid → HCID 78322299, compound

HRID 1051295Notes

Reaction equation

HRID 1051295 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]([CH3:21])[CH3:20])=[C:14]([N:22]3[CH:26]=[CH:25][N:24]=[N:23]3)[CH:13]=2)[S:5][C:6]=1[C:7]([O:9]CC)=[O:8].[OH-].[Na+].Cl.O>O1CCCC1.CO>[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]([CH3:21])[CH3:20])=[C:14]([N:22]3[CH:26]=[CH:25][N:24]=[N:23]3)[CH:13]=2)[S:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 118555038HCID 118555038, compound

Product 1

HCID 78322299HCID 78322299, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A reaction mixture solution prepared by dissolving 501 mg of ethyl 4-methyl-2-[4-(propan-2-yloxy)-3-(1H-1,2,3-triazol-1-yl)phenyl]-1,3-thiazole-5-carboxylate in 10 mL of a mixed solution of tetrahydrofuran/methanol=1/1 and adding 1.35 mL of 2 M sodium hydroxide aqueous solution was stirred at room temperature for 3 hours. After the addition of 1.35 mL of 2 M hydrochloric acid to the reaction mixture solution under stirring, 8 mL of water was added and extraction was performed using 20 mL of ethyl acetate. The organic phase was concentrated, followed by purifying by a conventional method to obtain 415 mg of 4-methyl-2-[4-(propan-2-yloxy)-3-(1H-1,2,3-triazol-1-yl)phenyl]-1,3-thiazole-5-carboxylic acid.

Workup

  1. customA reaction mixture solution prepared
  2. stirringunder stirring
  3. extractionextraction
  4. concentrationThe organic phase was concentrated
  5. customby purifying by a conventional method

Sources & evidence

ORD record
ord-27a5cd5e38af4eb0932ec6b74a6a31a1
Source dataset
uspto-grants-2016_07
Patent number
US09388174B2

Reaction notes

Loading…