Thionyl Chloride → N-(2-chloroethyl)-4-fluoro-2-nitrobenzamide

HRID 1156330Notes

Reaction equation

HRID 1156330 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([NH:8][CH2:9][CH2:10]O)=[O:7])=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=1.S(Cl)([Cl:19])=O>ClC(Cl)Cl>[Cl:19][CH2:10][CH2:9][NH:8][C:6](=[O:7])[C:5]1[CH:12]=[CH:13][C:2]([F:1])=[CH:3][C:4]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 202789664-fluoro-N-(2-hydroxyethyl)-2-nitrobenzamide

Product 1

HCID 20278955N-(2-chloroethyl)-4-fluoro-2-nitrobenzamideYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 28 parts of 4-fluoro-N-(2-hydroxyethyl)-2-nitrobenzamide, 40 parts of thionyl chloride and 150 parts of trichloromethane is stirred and refluxed for 2 hours. After cooling, the precipitated product is filtered off and dried, yielding 24.5 parts (83%) of N-(2-chloroethyl)-4-fluoro-2-nitrobenzamide.

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated product is filtered off
  4. customdried

Sources & evidence

ORD record
ord-c69bea10de1049e4bde92ac30d02d961
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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