Thionyl Chloride → 2,6-Dichloro-4-cyano-N-(3,5-difluoropyridin-4-yl)-benzimidoyl chloride

HRID 2366276Notes

Reaction equation

HRID 2366276 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[C:15]([Cl:21])[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]=[C:17]([C:19]#[N:20])[CH:16]=[C:15]([Cl:21])[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 668013412,6-Dichloro-4-cyano-N-(3,5-difluoropyridin-4-yl)-benzamide

Product 1

HCID 867233192,6-Dichloro-4-cyano-N-(3,5-difluoropyridin-4-yl)-benzimidoyl chloride

Conditions

Temperature
85 °C

Procedure

A stirred suspension of 2,6-dichloro-4-cyano-N-(3,5-difluoropyridin-4-yl)-benzamide (1.35 g, 4.12 mmol) in thionyl chloride (14 mL) was heated at 85° C. for 5 hours and then at 80° C. for 56 hours under a nitrogen atmosphere. After cooling to room temperature, the volatiles were removed under reduced pressure to afford the title compound as an orange solid (1.5 g, quantitative). LCMS (Method D): RT=4.01 min, m/z: 346 [M+H+].

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-377f6a9ea48641e2af6a687ab2fb8c8c
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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