6-Chloroimidazo[2,1-b][1,3]thiazole-5-carbaldehyde → 6-Chloro-imidazo[2,1-b]thiazole-5-carboxylic acid

HRID 560305Notes

Reaction equation

HRID 560305 reaction equation
Cl([O-])=O.[Na+].[OH2:5].O.P([O-])(O)(O)=O.[Na+].[Cl:13][C:14]1[N:15]=[C:16]2[N:20]([C:21]=1[CH:22]=[O:23])[CH:19]=[CH:18][S:17]2>O.C(O)(C)(C)C>[Cl:13][C:14]1[N:15]=[C:16]2[N:20]([C:21]=1[C:22]([OH:5])=[O:23])[CH:19]=[CH:18][S:17]2

Participants

6

Reactant 3

HCID 3299506-Chloroimidazo[2,1-b][1,3]thiazole-5-carbaldehydeHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, Dihydrate

Product 1

HCID 3299776-Chloro-imidazo[2,1-b]thiazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of sodium chlorite (230 mmol) and sodium dihydrogen phosphate dihydrate (176 mmol) in water (195 mL) is added dropwise to a solution of 6-chloro-imidazo[2,1-b]thiazole-5-carbaldehyde (26.8 mmol) in tert.-butanol (195 mL) and the mixture is stirred for 8 h at RT. The solvents are partially removed in vacuo and the obtained precipitate is filtered off. The filtrate is made acidic and the obtained precipitate is filtered off to give the desired product as a white solid.

Workup

  1. customThe solvents are partially removed in vacuo
  2. filtrationthe obtained precipitate is filtered off
  3. filtrationthe obtained precipitate is filtered off

Sources & evidence

ORD record
ord-a4c2b60627294f8090a8f0ede8077b7c
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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