Hydrochloric Acid → Azole benzene derivative 2

HRID 1051297Notes

Reaction equation

HRID 1051297 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]=[N: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]=[N: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 118555064ethyl 4-methyl-2-[4-(propan-2-yloxy)-3-(1H-1,2,3,4-tetrazol-1-yl)phenyl]-1,3-thiazole-5-carboxylate

Product 1

HCID 78322305Azole benzene derivative 2Yield 88%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A reaction mixture solution prepared by dissolving 1.13 g of ethyl 4-methyl-2-[4-(propan-2-yloxy)-3-(1H-1,2,3,4-tetrazol-1-yl)phenyl]-1,3-thiazole-5-carboxylate in 15 mL of a mixed solution of tetrahydrofuran/methanol=1/1 and adding 3.0 mL of 2 M sodium hydroxide aqueous solution to the mixture was stirred at room temperature for 3 hours. After the addition of 3.0 mL of 2 M hydrochloric acid to the reaction solution under stirring, 7 mL of water was added and extraction was performed using 30 mL of ethyl acetate. The organic layer was concentrated, followed by purifying by a conventional method to obtain 920 mg of 4-methyl-2-[4-(propan-2-yloxy)-3-(1H-1,2,3,4-tetrazol-1-yl)phenyl]-1,3-thiazole-5-carboxylic acid.

Workup

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

Sources & evidence

ORD record
ord-a5a28193dbe64b7b8049a91513de446d
Source dataset
uspto-grants-2016_07
Patent number
US09388174B2

Reaction notes

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