Lithium Hydroxide → 6-(4-Fluorophenyl)-3-methylimidazo[2,1-b][1,3]thiazole-2-carboxylic acid

HRID 659144Notes

Reaction equation

HRID 659144 reaction equation
[OH-].[Li+].C([O:5][C:6]([C:8]1[S:12][C:11]2=[N:13][C:14]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[CH:15][N:10]2[C:9]=1[CH3:23])=[O:7])C>C(O)C.O>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2[N:13]=[C:11]3[N:10]([CH:15]=2)[C:9]([CH3:23])=[C:8]([C:6]([OH:7])=[O:5])[S:12]3)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 19224540Ethyl 6-(4-fluorophenyl)-3-methylimidazo[2,1-b][1,3]thiazole-2-carboxylate

Product 1

HCID 226936536-(4-Fluorophenyl)-3-methylimidazo[2,1-b][1,3]thiazole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To lithium hydroxide (184.4 mg, 7.7 mmol) in 100 ml of ethanol and 100 ml of water was added 6-(4-fluoro-phenyl)-3-methyl-imidazo[2,1-b]thiazole-2-carboxylic acid ethyl ester (example 1, 2.13 g, 7 mmol). After stirring 24 hours at RT the mixture was filtered and the filtrate partially evaporated. The aqueous solution was acidified with hydrochloric acid to pH 4 and the separated product filtered and dried. Yield: 1.11 g (57%). MS: M+H+=277.01.

Workup

  1. filtrationwas filtered
  2. customthe filtrate partially evaporated
  3. filtrationthe separated product filtered
  4. customdried

Sources & evidence

ORD record
ord-44c0761c873a48eebc75fbd906d787c4
Source dataset
uspto-grants-2011_12
Patent number
US08080569B2

Reaction notes

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