Thionyl Chloride → HCID 86668992, compound

HRID 2366207Notes

Reaction equation

HRID 2366207 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[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]([Cl: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 86723307HCID 86723307, compound

Product 1

HCID 86668992HCID 86668992, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2,6-dichloro-N-(2-chloro-3-fluoropyridin-4-yl)benzamide (1.12 g, 3.5 mmol) and thionyl chloride (10 mL) was heated under reflux for 18 hours then cooled to ambient temperature. The reaction mixture was diluted with toluene (10 mL) and concentrated under reduced pressure to afford the title compound as a pale brown solid (1.23 g, quant. yield). 1H NMR (400 MHz, CDCl3): δ 8.23 (d, J=5.1 Hz, 1H), 7.45-7.44 (m, 2H), 7.38 (dd, J=9.4, 6.5 Hz, 1H), 6.98 (t, J=5.1 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-1fff0b5b68b74742bde502178a88ace9
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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