Thionyl Chloride → HCID 86723304, compound

HRID 2366196Notes

Reaction equation

HRID 2366196 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[CH:12]=[CH:11][N:10]=[C:9]([Cl:13])[C:8]=1[F:14])=O.S(Cl)([Cl:22])=O>C1(C)C=CC=CC=1>[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[CH:12]=[CH:11][N:10]=[C:9]([Cl:13])[C:8]=1[F:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86723303HCID 86723303, compound

Product 1

HCID 86723304HCID 86723304, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-chloro-N-(2-chloro-3-fluoro-pyridine-4-yl)-6-fluorobenzamide (600 mg, 2 mmol) and thionyl chloride (5 mL) was heated under reflux for 16 hours then cooled to ambient temperature. The reaction mixture was diluted with toluene (6 mL) and concentrated to dryness under reduced pressure to give the desired compound as a brown oil (650 mg, quant. yield). 1H NMR (400 MHz, CDCl3): δ 8.23 (d, J=5.1 Hz, 1H), 7.44 (td, J=8.3, 5.6 Hz, 1H), 7.33 (d, J=8.2 Hz, 1H), 7.16 (t, J=8.7 Hz, 1H), 6.97 (t, J=5.1 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-986d213f9ea347d4b51f7d81b05e4946
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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