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

HRID 2064749Notes

Reaction equation

HRID 2064749 reaction equation
[O-:1]Cl.[Na+].[Cl:4][C:5]1[N:6]=[C:7]2[N:11]([C:12]=1[CH:13]=[O:14])[CH:10]=[CH:9][S:8]2>O.C(O)(C)(C)C>[Cl:4][C:5]1[N:6]=[C:7]2[N:11]([C:12]=1[C:13]([OH:1])=[O:14])[CH:10]=[CH:9][S:8]2

Participants

5

Reactant 2

HCID 3299506-Chloroimidazo[2,1-b][1,3]thiazole-5-carbaldehydeHCID 23665760Sodium Hypochlorite

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 NaOCl (230 mmol) and NaH2PO4 (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. LC-MS: tR=0.67 min; [M+H]+=202.9.

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-f8a3397c310d4681ac1b2a38b5f3b71a
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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