Lithium Hydroxide → 2-(6-Benzyloxy-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid

HRID 1667731

Reaction equation

HRID 1667731 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([N:11]2[C:15]3[CH:16]=[C:17]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)=[N:8][C:7]=1[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=1)=[O:5])C.O1CCCC1.[OH-].[Li+]>O>[CH2:21]([O:20][C:17]1[CH:18]=[CH:19][C:14]2[N:13]=[CH:12][N:11]([C:9]3[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=4)[N:8]=3)[C:15]=2[CH:16]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 674458212-(6-Benzyloxy-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 674440732-(6-Benzyloxy-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acidYield 100.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.5 g (7.14 mmole) of 2-(6-benzyloxy-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester (I.25a), 50 mL of tetrahydrofuran, 50 mL of water and 0.857 g (35.7 mmole) of lithium hydroxide was heated at 60 degrees for 3 hours. The mixture was concentrated under reduced pressure, and then 100 mL of water was added. The pH was adjusted to ca. 3-4 by the addition of hydrochloric acid. The resulting precipitate was collected by filtration to give 3.3 g of 2-(6-benzyloxy-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid (I.25b) as a white solid.

Workup

  1. temperaturewas heated at 60 degrees for 3 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. addition100 mL of water was added
  4. additionby the addition of hydrochloric acid
  5. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-7dcb09516d0045e6ad982201ccbf4e4e
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Linked notes

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