Thionyl Chloride → HCID 86669010, compound

HRID 2366267Notes

Reaction equation

HRID 2366267 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[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:22])=O>>[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:3]=1[C:4]([Cl:22])=[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 66801411HCID 66801411, compound

Product 1

HCID 86669010HCID 86669010, compound

Conditions

Temperature
85 °C

Procedure

A stirred suspension of 2,6-dichloro-N-(3,5-difluoropyridin-4-yl)-benzamide (14.5 g, 47.8 mmol) in thionyl chloride (130 mL) was heated at 85° C. for 20 hours and then at 90° C. for 26 hours under argon. After cooling to room temperature, the volatiles were removed under reduced pressure, azeotroped with toluene (×3) to afford the title compound as a yellow solid (15.7 g, quantitative). LCMS (Method D): RT=4.16 min, m/z: 321 [M+H+].

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe volatiles were removed under reduced pressure
  3. customazeotroped with toluene (×3)

Sources & evidence

ORD record
ord-7b88d9fc32424f1eaf57b4e05a9287b0
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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