Methane → 2-(3-Chloro-phenoxy)-thiazole-4-carboxylic acid

HRID 1938142

Reaction equation

HRID 1938142 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[S:9][CH:10]=1)=[O:5])C.[OH-].[Na+].C>O>[Cl:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[O:11][C:8]1[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 14798Sodium HydroxideHCID 214686012-(3-Chloro-phenoxy)-thiazole-4-carboxylic acid ethyl ester

Product 1

HCID 214686062-(3-Chloro-phenoxy)-thiazole-4-carboxylic acidYield 94.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 26,36g (92.9 mmol) ethyl-2-(3-chlorophenoxy)thiazole-4-carboxylate (prepared analogously to the procedures of Example 1c), 7.5 g (187.5 mmol) NaOH and 300 ml of water was stirred 1 hour at 60° C. and 16 hours at room temperature. After adding a small amount of charcoal the yellow solution was stirred 10 minutes at room temperature and the charcoal separated by silica gel filtration. The filtrate was acidified with conc. HCl and the precipitate was collected and dried to give 22.5 g (94.7%) of 2-(3-chlorophenoxy)thiazole-4-carboxylic acid of m.p. 135°-137° C.

Workup

  1. stirringwas stirred 10 minutes at room temperature
  2. customthe charcoal separated by silica gel filtration
  3. customthe precipitate was collected
  4. customdried

Sources & evidence

ORD record
ord-9eeb861e785142f8b5a100dcaf7f3551
Source dataset
uspto-grants-1997_12
Patent number
US05693594

Linked notes

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