Thionyl Chloride → HCID 86669019, compound

HRID 2366289Notes

Reaction equation

HRID 2366289 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[C:3]=1[C:4]([NH:6][C:7]1[C:12]([F:13])=[CH:11][N:10]=[CH:9][C:8]=1[F:14])=O.S(Cl)([Cl:24])=O>>[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[C:3]=1[C:4]([Cl:24])=[N:6][C:7]1[C:12]([F:13])=[CH:11][N:10]=[CH:9][C:8]=1[F:14]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 66801651HCID 66801651, compound

Product 1

HCID 86669019HCID 86669019, compound

Procedure

A mixture of 2-chloro-N-(3,5-difluoropyridin-4-yl)-6-nitrobenzamide (5.25 g, 16.7 mmol) in thionyl chloride (40 mL) was heated under reflux for 18 hours under a nitrogen atmosphere. After cooling to room temperature, the volatiles were removed under reduced pressure and the resultant residue was azeotroped with toluene (×3) to afford the title compound as a yellow/brown solid (5.5 g, quantitative). LCMS (Method D): RT=3.77 min, m/z: 332 [M+H+].

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours under a nitrogen atmosphere
  3. customthe volatiles were removed under reduced pressure
  4. customthe resultant residue was azeotroped with toluene (×3)

Sources & evidence

ORD record
ord-925b347edd6d4332bca4e9eb8590fbac
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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