Methanol → 4-[(3-Chloropropyl)sulfanyl]benzene-1,2-diamine

HRID 1730816Notes

Reaction equation

HRID 1730816 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([S:11][CH2:12][CH2:13][CH2:14][Cl:15])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.CO.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[NH2:6][C:5]1[CH:7]=[CH:8][C:9]([S:11][CH2:12][CH2:13][CH2:14][Cl:15])=[CH:10][C:4]=1[NH2:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 24489Sodium DithioniteHCID 214502084-[(3-Chloropropyl)sulfanyl]-2-nitroaniline

Product 1

HCID 214502104-[(3-Chloropropyl)sulfanyl]benzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6 G. of 2-nitro-4-(3-chloropropylthio)aniline is treated in 120 ml. of methanol and 120 ml. of water with 30 g. of sodium hydrosulfite (Na2S2O4) on the steam bath for about 5 minutes. The reaction mixture is concentrated under vacuum and extracted well with chloroform. Evaporation of the dried extract affords 1,2-diamino-4-(3-chloropropylthio)benzene.

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. extractionextracted well with chloroform
  3. customEvaporation of the dried
  4. extractionextract

Sources & evidence

ORD record
ord-f97df387bb0b4a9eaf68bada19a69022
Source dataset
uspto-grants-1976_11
Patent number
US03993768

Reaction notes

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