Thionyl Chloride → 2,6-dichloro-N-(3,5-difluoropyridin-4-yl)-4-iodobenzimidoyl chloride

HRID 2366315Notes

Reaction equation

HRID 2366315 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([I:19])[CH:16]=[C:15]([Cl: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:23])=O>>[Cl:1][C:2]1[CH:18]=[C:17]([I:19])[CH:16]=[C:15]([Cl:20])[C:3]=1[C:4]([Cl:23])=[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 668018812,6-dichloro-N-(3,5-difluoropyridin-4-yl)-4-iodobenzamide

Product 1

HCID 866690292,6-dichloro-N-(3,5-difluoropyridin-4-yl)-4-iodobenzimidoyl chloride

Procedure

A mixture of 2,6-dichloro-N-(3,5-difluoropyridin-4-yl)-4-iodobenzamide (21.3 g, 49.7 mmol) in thionyl chloride (118 mL) was heated under reflux for 20 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) and dried under vacuum to afford the title compound as a brown solid (22.4 g, quantitative). LCMS (Method E): RT=4.69 min, m/z: 448 [M+H+].

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours under a nitrogen atmosphere
  3. customthe volatiles were removed under reduced pressure
  4. customthe resultant residue was azeotroped with toluene (×3)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d0138dbfefa9494fb4715a93a951a32f
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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