Hydrochloric Acid → 2-(4-Hydroxyphenyl)-1,3-thiazole-4-carboxylic acid

HRID 471795

Reaction equation

HRID 471795 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[S:10])[NH2:9])=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:14][C:15](=O)[C:16]([OH:18])=[O:17].Cl>O.CO>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:10][CH:14]=[C:15]([C:16]([OH:18])=[O:17])[N:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 70684Bromopyruvic AcidHCID 27593444-Hydroxythiobenzamide

Product 1

HCID 1357678972-(4-Hydroxyphenyl)-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

4-Hydroxybenzenecarbothioamide (1.53 g, 10 mmol) and potassium hydroxide (1.50 g, 26.8 mmol) were dissolved in a mixture of 60 ml of water and 15 ml of methanol. A solution of bromopyruvic acid (1.67 g, 10 mmol) in 10 ml of methanol was added dropwise at room temperature. The resulting mixture was heated to reflux for 1.5 h, cooled to room temperature, poured into 100 ml of water and adjusted with 0.2N HCl solution to pH2. The mixture was placed in a refrigerator for 15 h. The title compound was obtained by filtration as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.82 (d, 2H), 7.78 (d, 2H), 8.37 (s, 1H), 10.05 (s, 1H), 13.00 (s, 1H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 1.5 h

Sources & evidence

ORD record
ord-a7d320b1c39c49749b30377a2304fbb8
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Linked notes

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