Chloroform → N-[2-Nitro-4-(phenylmethanesulfinyl)phenyl]acetamide

HRID 1679442Notes

Reaction equation

HRID 1679442 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][C:6]=1[N+:19]([O-:21])=[O:20])(=[O:3])[CH3:2].C(Cl)(Cl)Cl.C(OO)(=[O:28])C>CO>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:28])=[CH:7][C:6]=1[N+:19]([O-:21])=[O:20])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6585Peracetic AcidHCID 20362823N-[4-(Benzylsulfanyl)-2-nitrophenyl]acetamide

Product 1

HCID 20362831N-[2-Nitro-4-(phenylmethanesulfinyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.42 G. 1-acetamido-2-nitro-4-benzylthiobenzene in 25 ml. chloroform is treated at -20° to -15° C with 1.6 g. 40% peracetic acid in 2 ml. methanol. The mixture is allowed to warm slowly to room temperature, held for 6 hours and washed with sodium bisulfite solution and sodium bicarbonate solution, dried and stripped. The residue is recrystallized from methanol giving 1-acetamido-2-nitro-4-benzylsulfinylbenzene.

Workup

  1. washwashed with sodium bisulfite solution and sodium bicarbonate solution
  2. customdried
  3. customThe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-71489e858a034260879f2a10660062c1
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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