Thioglycolic Acid → HCID 11448664, compound

HRID 1479702Notes

Reaction equation

HRID 1479702 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].CN(C=O)C.[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 6228DimethylformamideHCID 86534-Chlorobenzophenone2×HCID 14798Sodium Hydroxide

Product 1

HCID 11448664HCID 11448664, compoundYield 75.2%

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 DMF 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 precipitates, filtering to obtain crude products, and the weight after drying is 58 g; the dried crude products are recrystallized in dichloroethane to obtain 52 g white crystal, with a yield of 75% and a melting point of 130-132° C. 1H-NMR data (solvent DMSO-d6): δ3.796 ppm, s, 2H; δ7.402, 7.429 ppm, d, 2H; δ7.451, 7.476, 7.501 ppm, t, 2H; δ7.567, 7.590, 7.614 ppm, t, 1H; δ7.740, 7.767 ppm, d, 2H; δ7.753, 7.775 ppm, d, 2H).

Workup

  1. customto obtain a solution
  2. temperatureHeating the solution
  3. extractionwater insoluble substances are extracted with 100 ml methylbenzene
  4. customsome solid substances precipitates
  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-f61f9364724144b48a09fc0a652367b3
Source dataset
uspto-grants-2016_08
Patent number
US09409861B2

Reaction notes

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