Hydrogen Peroxide → HCID 22237059, compound

HRID 1744008Notes

Reaction equation

HRID 1744008 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])=[CH:4][CH:3]=1.[OH:19]O.CSC>C(O)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH2:9][C:10]([NH:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:11])=[O:19])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 1068Dimethyl SulfideHCID 22237044HCID 22237044, compound

Product 1

HCID 22237059HCID 22237059, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6.0 g (23.2 mmol) of 2-(4-hydroxyphenylthio)acetoanilide and 50 mL of acetic acid were added under a room temperature into a 100 mL flask with four inlets and attached with a stirrer and a thermometer. To the resultant solution, 2.8 g (24.7 mmol) of 30k aqueous solution of hydrogen peroxide was added, and the resultant solution was stirred for 12 hours at a room temperature. Following to the completion of the reaction, 0.5 g of dimethyl sulfide was added into the solution, and then, the solution was extracted with MIBK. The MIBK layer was washed several times with water, and followed by washing with sodium hydrogencarbonate. The MIBK in the solution was distilled out under reduced pressure, and the resultant residue was subjected to recrystallization with MIBK to obtain 5.9 g of 2-(4-hydroxyphenylsulfinyl)acetoanilide. The yield was 93% and the melting point of the compound was in a range of 208 to 210° C.

Workup

  1. customattached with a stirrer
  2. additionwas added into the solution
  3. extractionthe solution was extracted with MIBK
  4. washThe MIBK layer was washed several times with water
  5. washby washing with sodium hydrogencarbonate
  6. distillationThe MIBK in the solution was distilled out under reduced pressure
  7. customthe resultant residue was subjected to recrystallization with MIBK

Sources & evidence

ORD record
ord-06194fffc6e041a7a7b4d9186c32e2d7
Source dataset
uspto-grants-2006_03
Patent number
US07012159B1

Reaction notes

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