Hydrochloric Acid → 4-Carboxymethyl-2-(4-chloro-phenyl)-thiazole-5-carboxylic acid

HRID 554852Notes

Reaction equation

HRID 554852 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:18][C:19]([O:21]CC)=[O:20])=[O:5])C.[OH-].[Na+].Cl>CCO>[C:19]([CH2:18][C:7]1[N:8]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[S:10][C:6]=1[C:4]([OH:5])=[O:3])([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 674592172-(4-Chloro-phenyl)-4-ethoxycarbonylmethyl-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 674612304-Carboxymethyl-2-(4-chloro-phenyl)-thiazole-5-carboxylic acidYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve 2-(4-chloro-phenyl)-4-ethoxycarbonylmethyl-thiazole-5-carboxylic acid ethyl ester (99 g, 280 mmol) in EtOH (500 mL) and add 2 M NaOH (700 mL, 1400 mmol). Heat the mixture to 50° C. for 1.5 h, then cool the solution in an ice bath, and treat with 2.5 M HCl (1 L) and stir for 2 h. Collect the precipitate by filtration, washing with 50% EtOH/water (500 mL), and then washing with water (1 L). Dry in a vacuum oven overnight at 45° C. to give 80.2 g (95%) of the title compound. 1H NMR (DMSO-d6, 500 MHz): δ 13.66 (br s, 1H), 12.55 (br s, 1H), 8.01 (d, 2H, J=8.6), 7.60 (d, 2H, J=8.9), 4.11 (s, 2H).

Workup

  1. temperaturecool the solution in an ice bath
  2. customCollect the precipitate
  3. filtrationby filtration
  4. washwashing with 50% EtOH/water (500 mL)
  5. washwashing with water (1 L)
  6. customDry in a vacuum oven overnight at 45° C.

Sources & evidence

ORD record
ord-478e7502e46e46969a699ad22b59820d
Source dataset
uspto-grants-2011_11
Patent number
US08049013B2

Reaction notes

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