Thionyl Chloride → HCID 86668994, compound

HRID 2366210Notes

Reaction equation

HRID 2366210 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[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]([Cl: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 86723308HCID 86723308, compound

Product 1

HCID 86668994HCID 86668994, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2,6-dichloro-N-(2-chloro-3-fluoro-pyridin-4-yl)-4-cyano-benzamide (1.2 g, 3.4 mmol) and thionyl chloride (12.5 mL) was heated under reflux for 18 hours then cooled to ambient temperature. The reaction mixture was diluted with toluene (10 mL) and concentrated to dryness under reduced pressure to afford the title compound as a white solid (1.23 g, 97% yield). 1H NMR (400 MHz, CDCl3): δ 8.25 (d, J=5.1 Hz, 1H), 7.75 (s, 2H), 6.97 (t, J=5.1 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-702019a27f1d4a6eb8e2dfc2af0ac5f2
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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