Hydrogen Peroxide → Acetamide, 2-(((4-chlorophenyl)methyl)sulfinyl)-N-hydroxy-

HRID 28167Notes

Reaction equation

HRID 28167 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][S:7][CH2:8][C:9]([NH:11][OH:12])=[O:10])=[CH:4][CH:3]=1.[OH:15]O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][S:7]([CH2:8][C:9]([NH:11][OH:12])=[O:10])=[O:15])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 54399917p-Chlorobenzylmercaptoacetohydroxamic acid

Product 1

HCID 3049612Acetamide, 2-(((4-chlorophenyl)methyl)sulfinyl)-N-hydroxy-Yield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
50 °C

Procedure

31.7 g (0.091 mol) of p-chlorobenzylmercaptoacetohydroxamic acid are mixed with 100 ml of anhydrous acetic acid and 9.1 ml of hydrogen peroxide of 110 volumes strength are added. The temperature, which is 20° C. at the start, rises and solution of the precipitate formed is also observed. The temperature is maintained at 50° C. and after several minutes it is found that the sulphinyl derivative sets solid. 50 ml of acetic acid are now added and the temperature is kept at 50° C. for 1 hour whilst stirring vigorously. The mixture is cooled and the p-chlorobenzylsulphinyl-acetohydroxamic acid is filtered off. This acid is recrystallised from acetic acid and filtered off, the precipitate is washed with water and with ethanol, and dried, and 31.9 g of CRL 40,411 are collected. Yield 85%; instantaneous melting point 210° C. (with decomposition).

Workup

  1. additionare added
  2. customis 20° C. at the start
  3. customsolution of the precipitate formed
  4. temperatureThe mixture is cooled
  5. filtrationthe p-chlorobenzylsulphinyl-acetohydroxamic acid is filtered off
  6. customThis acid is recrystallised from acetic acid
  7. filtrationfiltered off
  8. washthe precipitate is washed with water and with ethanol
  9. customdried
  10. custom31.9 g of CRL 40,411 are collected

Sources & evidence

ORD record
ord-4fe72f7d2c974fcd9f4fea9ce41b54ae
Source dataset
uspto-grants-1980_09
Patent number
US04225617

Reaction notes

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