Thionyl Chloride → HCID 21250146, compound

HRID 1531734Notes

Reaction equation

HRID 1531734 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1)#[N:2].S(Cl)(Cl)=O.[NH2:17][C:18]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([NH:17][C:18]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:19]=2[C:20]([O:22][CH3:23])=[O:21])=[O:12])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 795874-Cyanophenylacetic acidHCID 2777346methyl 2-amino-5-nitrobenzoate

Product 1

HCID 21250146HCID 21250146, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.8 g (3 mmol) of (4-cyano-phenyl)-acetic acid are suspended in 25 ml of methylene chloride and refluxed for 15 minutes after the addition of 5 ml thionyl chloride. The solvent is distilled off, the residue dissolved in 100 ml chlorobenzene and after the addition of 4.9 g (2.5 mmol) of methyl 2-amino-5-nitro-benzoate refluxed for 2 hours. Three-quarters of the volume of chlorobenzene is distilled off and the residue is combined with ether/petroleum ether. The crystalline product is suction filtered and dried.

Workup

  1. temperaturerefluxed for 15 minutes
  2. distillationThe solvent is distilled off
  3. dissolutionthe residue dissolved in 100 ml chlorobenzene
  4. temperaturerefluxed for 2 hours
  5. distillationThree-quarters of the volume of chlorobenzene is distilled off
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-04d6c8dc5a0c423bb91edfe18b39738f
Source dataset
uspto-grants-2001_03
Patent number
US06200976B1

Reaction notes

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