Thioglycolic Acid → HCID 11448664, compound

HRID 2174412Notes

Reaction equation

HRID 2174412 reaction equation
Cl[C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[SH:16][CH2:17][C:18]([OH:20])=[O:19].CC(N(C)C)=O.[OH-].[Na+]>O>[C:18]([CH2:17][S:16][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1)([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 1133Thioglycolic AcidHCID 86534-Chlorobenzophenone2×HCID 14798Sodium HydroxideHCID 31374Dimethylacetamide

Product 1

HCID 11448664HCID 11448664, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
107.5 °C

Procedure

55 g 4-chloro benzophenone and 24 g mercaptoacetic acid are added into a 500 ml three-neck flask, and are dissolved with 350 ml DME (dimethyl acetamide) to obtain a solution, and then 23 g solid sodium hydroxide is added into the solution. Heating the solution to reflux (105-110° C.), and starting to cool the solution when the content of 4-chloro benzophenone detected by HPLC is less than 1%. The reaction solution is added into 500 ml water, and then water insoluble substances are extracted with 100 ml methylbenzene. Concentrated hydrochloric acid is used to regulate the pH value of the aqueous phase to 3-4, then some solid substances precipitate, filtering to obtain crude products, and the weight after drying is 60 g; the dried crude products are recrystallized in dichloroethane to obtain 55.3 g white crystal, and the yield was 80%.

Workup

  1. customto obtain a solution
  2. temperatureHeating the solution
  3. extractionwater insoluble substances are extracted with 100 ml methylbenzene
  4. customsome solid substances precipitate
  5. filtrationfiltering
  6. customto obtain crude products
  7. customthe weight after drying
  8. customthe dried crude products
  9. customare recrystallized in dichloroethane

Sources & evidence

ORD record
ord-9c26f576e79f4ba2bf40ffca3d50a13c
Source dataset
uspto-grants-2015_06
Patent number
US09061979B2

Reaction notes

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