Thionyl Chloride → HCID 86669016, compound

HRID 2366280Notes

Reaction equation

[Br: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>>[Br: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

Reactant 2

HCID 24386Thionyl Chloride

HCID 86723320HCID 86723320, compound

Product 1

HCID 86669016HCID 86669016, compoundYield 83%

Procedure

A stirred solution of 2-bromo-6-chloro-N-(2-chloro-3-fluoropyridin-4-yl)-benzamide (4.8 g, 13.2 mmol) in thionyl chloride (100 mL) was heated at 100° C. for 18 hours 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 30% diethyl ether in pentane to afford the title compound as a pale yellow solid (4.2 g, 83% yield). LCMS (Method D): RT=4.47 min, m/z: 383 [M+H+].

Workup

customthe volatiles were removed under reduced pressure
customthe resultant residue was purified by column chromatography on silica gel eluting with 30% diethyl ether in pentane

Sources & evidence

ORD record: ord-0ce393258c4c42a9a98164cc7acc4a3a
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697708B2

Reaction notes

Loading…