Sodium Hydroxide → 2-(4-Chloro-phenyl)-4-(2,2-dimethoxy-ethyl)-thiazole-5-carboxylic acid

HRID 554840Notes

Reaction equation

C[O:2][C:3]([C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[N:7][C:6]=1[CH2:17][CH:18]([O:21][CH3:22])[O:19][CH3:20])=[O:4].[OH-].[Na+]>CCO>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]2[S:9][C:5]([C:3]([OH:4])=[O:2])=[C:6]([CH2:17][CH:18]([O:21][CH3:22])[O:19][CH3:20])[N:7]=2)=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Mix 2-(4-chloro-phenyl)-4-(2,2-dimethoxy-ethyl)-thiazole-5-carboxylic acid methyl ester (3.6 g, 10.5 mmol) in EtOH (40 mL) and then add 2 M NaOH (6.8 mL). Stir the slurry mechanically overnight and then concentrate in vacuo. Dissolve the solid in water (40 mL), cool to 0° C., and adjust the pH to 5-6 with 1 N HCl (13 mL). Stir the slurry for 15 min, collect the precipitate, and wash the solid with water (4×20 mL). Dry the solid in a vacuum oven overnight to give 3.3 g (96%) of the title compound. ES/MS m/z (35Cl) 326.0 [M−1]−.

Workup

concentrationconcentrate in vacuo
dissolutionDissolve the solid in water (40 mL)
stirringStir the slurry for 15 min
customcollect the precipitate
washwash the solid with water (4×20 mL)
customDry the solid in a vacuum oven overnight

Sources & evidence

ORD record: ord-5ec61726b0bb42b9ba82529618dd7266
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08049013B2

Reaction notes

Loading…