Chloroform → HCID 20371014, compound

HRID 616117Notes

Reaction equation

HRID 616117 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH:13]=[CH2:14])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])(=[O:3])[CH3:2].C(Cl)(Cl)Cl.C(OO)(=[O:24])C>CO>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:12][CH:13]=[CH2:14])=[O:24])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6585Peracetic AcidHCID 14273283N-{2-Nitro-4-[(prop-2-en-1-yl)sulfanyl]phenyl}acetamide

Product 1

HCID 20371014HCID 20371014, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.0 G. of 1-acetamido-2-nitro-4-(prop-2-en-1-yl-thio)benzene, prepared according to Example I, in 30 ml. chloroform is cooled to -15° C. and treated with a solution of 2.5 g. of 40% peracetic acid in 4 ml. methanol. After the addition, the temperature is allowed to rise slowly to 20° C whereupon the solution is washed with sodium bisulfite solution and then with sodium bicarbonate solution. The product is isolated by evaporation of the solvent and purified to afford 1-acetamido-2-nitro-4-(prop-2-en-1-ylsulfinyl)benzene. This is treated with 20 ml. methanol and 10 ml. 5N aqueous sodium hydroxide at 20°-25° C. for one hour. The mixture is diluted with water and the crude product filtered off. Recrystallization yields 1-amino-2-nitro-4-(prop-2-en-1-ylsulfinyl)benzene.

Workup

  1. additiontreated with a solution of 2.5 g
  2. additionAfter the addition
  3. customto rise slowly to 20° C whereupon the solution
  4. washis washed with sodium bisulfite solution
  5. customThe product is isolated by evaporation of the solvent
  6. custompurified

Sources & evidence

ORD record
ord-c1b923daaf6e4fdaa4458f08f6fad051
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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