Thionyl Chloride → 2-Chloro-N-(2-chloro-3-fluoropyridin-4-yl)-4-cyano-6-fluorobenzimidoyl chloride

HRID 2366227Notes

Reaction equation

HRID 2366227 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[C:15]([F:21])[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:24])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[C:15]([F:21])[C:3]=1[C:4]([Cl:24])=[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 86723312HCID 86723312, compound

Product 1

HCID 867233132-Chloro-N-(2-chloro-3-fluoropyridin-4-yl)-4-cyano-6-fluorobenzimidoyl chlorideYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-chloro-N-(2-chloro-3-fluoro-pyridin-4-yl)-4-cyano-6-fluorobenzamide (0.805 g, 2.5 mmol) in thionyl chloride (7.5 mL) was heated under reflux for 65 h then cooled to ambient temperature. The reaction mixture was diluted with toluene and concentrated under reduced pressure to give the desired compound as a yellow solid (0.814 g, 96% yield). 1H NMR (300 MHz, CDCl3): δ 8.25 (d, J=5.1 Hz, 1H), 7.70-7.63 (m, 1H), 7.49 (dd, J=8.0, 1.0 Hz, 1H), 6.97 (t, J=5.0 Hz, 1H). LCMS (Method D): RT=4.09 min, m/z: 346 [M+H+].

Workup

  1. temperatureunder reflux for 65 h
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb522c024a064b17a2e70ca4d4e861c9
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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