Thionyl Chloride → HCID 12680455, compound

HRID 1896220Notes

Reaction equation

[O:1]=[C:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)=[O:6].[S:21](Cl)(Cl)=O>>[C:2]([C:3]1[S:21][N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:5](=[O:6])[CH:4]=1)(=[O:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 848829HCID 848829, compound

Product 1

HCID 12680455HCID 12680455, compoundYield 77%

Procedure

A solution of 4-oxo-4-phenyl-N-p-tolyl-butyramide 28 (252 mg, 0.944 mmol) in thionyl chloride (1 mL) was stirred for 16 h at room temperature. Excess thionyl chloride was removed under vacuum and the residue was purified by flash silica gel column chromatography (hexane:ethyl acetate=10:1 to 4:1) to give the compound 29 (216 mg, 77%). 1H-1-NMR (CDCl3, 300 MHz) δ 2.40 (s, 3H), 6.82 (s, 1H), 7.28 (m, 2H), 7.54 (m, 4H), 7.71 (m, 1H), 7.96 (m, 2H). HRMS: calculated for C17H14NO2S (M+H)+296.0745. Found 296.0762.

Workup

customExcess thionyl chloride was removed under vacuum
customthe residue was purified by flash silica gel column chromatography (hexane:ethyl acetate=10:1 to 4:1)

Sources & evidence

ORD record: ord-54b9f61c0b3b47b1ac2ae9041fd76576
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518957B2

Reaction notes

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