Thionyl Chloride → Benzenamine, N-(3-chloropropyl)-2-nitro-

HRID 258847Notes

Reaction equation

HRID 258847 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][CH2:12][CH2:13]O)([O-:3])=[O:2].S(Cl)([Cl:17])=O>ClC(Cl)Cl>[Cl:17][CH2:13][CH2:12][CH2:11][NH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 43125513-[(2-Nitrophenyl)amino]propan-1-ol

Product 1

HCID 10775026Benzenamine, N-(3-chloropropyl)-2-nitro-Yield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 39.2 parts of 3-(2-nitrophenyl)amino-1-propanol and 225 parts of trichloromethane are added dropwise 35.7 parts of sulfinyl chloride (exothermic reaction: temperature rises to 45° C). Upon completion, stirring is continued for 6 hours at reflux temperature. The reaction mixture is evaporated, yielding 43 parts (100%) of N-(3-chloropropyl)-2-nitrobenzenamine as a residue.

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture is evaporated

Sources & evidence

ORD record
ord-e1e6704771b549f290e68207002aa08e
Source dataset
uspto-grants-1977_07
Patent number
US04035369

Reaction notes

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