Thionyl Chloride → HCID 86723322, compound

HRID 2366286Notes

Reaction equation

[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[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>>[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[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

Reactant 2

HCID 24386Thionyl Chloride

HCID 86669018HCID 86669018, compound

Product 1

HCID 86723322HCID 86723322, compoundYield 87%

Procedure

A stirred solution of 2-chloro-N-(2-chloro-3-fluoropyridin-4-yl)-6-nitrobenzamide (4.27 g, 12.9 mmol) in thionyl chloride (60 mL) was heated at 85° C. for 2 days under a nitrogen atmosphere. After cooling to room temperature, the volatiles were removed under reduced pressure and the resultant residue was purified by column chromatography on silica gel eluting with 0-30% ethyl acetate in petroleum ether (40-60° C.), to afford the title compound as a cream solid (3.90 g, 87% yield). 1H NMR (400 MHz, CDCl3): δ 8.27-8.20 (m, 2H), 7.88 (dd, J=1.1, 8.1 Hz, 1H), 7.66 (t, J=8.2 Hz, 1H), 6.95 (t, J=5.2 Hz, 1H).

Workup

customthe volatiles were removed under reduced pressure
customthe resultant residue was purified by column chromatography on silica gel eluting with 0-30% ethyl acetate in petroleum ether (40-60° C.)

Sources & evidence

ORD record: ord-41426aa8ede44514ab275705aafd73b3
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697708B2

Reaction notes

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