Thionyl Chloride → N-(3-chloropropyl)-2-nitro-4-(trifluoromethyl)benzenamine

HRID 354951Notes

Reaction equation

HRID 354951 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[NH:14][CH2:15][CH2:16][CH2:17]O)([O-:3])=[O:2].S(Cl)([Cl:21])=O>ClC(Cl)Cl>[Cl:21][CH2:17][CH2:16][CH2:15][NH:14][C:5]1[CH:6]=[CH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 28475091-Propanol, 3-[[2-nitro-4-(trifluoromethyl)phenyl]amino]-

Product 1

HCID 20506352N-(3-chloropropyl)-2-nitro-4-(trifluoromethyl)benzenamine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 26 parts of 3-{[2-nitro-4-(trifluoromethyl)phenyl]amino}-1-propanol and 150 parts of trichloromethane are added dropwise 40 parts of sulfinyl chloride. Upon completion, stirring is continued overnight at reflux temperature. The reaction mixture is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5) as eluent. The pure fractions are collected and the eluent is evaporated, yielding N-(3-chloropropyl)-2-nitro-4-(trifluoromethyl)benzenamine as a residue.

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture is evaporated
  3. customThe residue is purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95:5) as eluent
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated

Sources & evidence

ORD record
ord-bde5098fa392448bb2f3cdea25f527a1
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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