Thioglycolic Acid → HCID 43328339, compound

HRID 1096994Notes

Reaction equation

HRID 1096994 reaction equation
[SH:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[K+].Cl[C:9]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:12]=[C:11]([CH3:20])[C:10]=1[CH:21]=O>C(O)C>[CH3:20][C:11]1[C:10]2[CH:21]=[C:2]([C:3]([OH:5])=[O:4])[S:1][C:9]=2[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:12]=1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 14797Potassium HydroxideHCID 121019265-chloro-3-methyl-1-(pyridin-2-yl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 43328339HCID 43328339, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 1.0-liter egg plant-type flask, mercaptoacetic acid (10.3 g, 0.15 mol) and potassium hydroxide (35.6 g, 0.54 mol) were added to an ethanol (600 mL) solution of 5-chloro-3-methyl-1-pyridin-2-yl-1H-pyrazole-4-carbaldehyde (30.0 g, 0.14 mol), and stirred for 2 hours with heating under reflux. Ethanol was removed from the reaction solution under reduced pressure, then the residue was diluted with water and made acidic with aqueous 5 N hydrochloric acid solution added thereto, and the formed precipitate was taken out through filtration, washed with methanol and ethyl acetate in that order, and dried under reduced pressure to obtain the title compound as a pale brown solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. customEthanol was removed from the reaction solution under reduced pressure
  4. additionthe residue was diluted with water
  5. additionadded
  6. filtrationthe formed precipitate was taken out through filtration
  7. washwashed with methanol and ethyl acetate in that order
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-132efd4f8c5444908ee776b5625f9c7e
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

Loading…