Thionyl Chloride → HCID 86669006, compound

HRID 2366258Notes

Reaction equation

HRID 2366258 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([F: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]([F: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 66801743HCID 66801743, compound

Product 1

HCID 86669006HCID 86669006, compound

Conditions

Temperature
100 °C

Procedure

A stirred suspension of 2-chloro-N-(3,5-difluoropyridin-4-yl)-6-fluorobenzamide (11.4 g, 0.04 mol) in thionyl chloride (100 mL) was heated at 100° C. for 18 hours. After cooling to room temperature, the volatiles were removed under reduced pressure. The resulting residue was azeotroped with toluene (100 mL). The crude residue was triturated with diethyl ether to afford the title compound as an off-white solid (12.1 g, quantitative). LCMS (Method E): RT=3.88 min, m/z: 305 [M+H+].

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe volatiles were removed under reduced pressure
  3. customThe resulting residue was azeotroped with toluene (100 mL)
  4. customThe crude residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-cbb90bdac3e644eeb0b08db2ac03750f
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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