Thionyl Chloride → N-Methyl 4-Nitrobenzimidoyl Chloride

반응식

[CH3:1][NH:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.S(Cl)([Cl:16])=O>>[CH3:1][N:2]=[C:3]([Cl:16])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1

참가 물질

반응물 2

HCID 24386Thionyl Chloride

HCID 347921N-Methyl-4-nitrobenzamide

생성물 1

HCID 12410498N-Methyl 4-Nitrobenzimidoyl Chloride수율 25.9%

실험 절차

N-Methyl 4-nitrobenzamide (30.0 g, 167 mmole) and thionyl chloride (256 g, 2.15 mole) were heated at reflux for five hours. The excess thionyl chloride was removed at ~15 mm Hg. Xylene was added to the reaction and distilled under reduced pressure to yield a solid which was recrystallized from petroleum ether to yield 8.6 g of the title compound as a light yellow solid, m.p. 67°-73° C.

후처리

temperatureat reflux for five hours
customThe excess thionyl chloride was removed at ~15 mm Hg
additionXylene was added to the reaction
distillationdistilled under reduced pressure
customto yield a solid which
customwas recrystallized from petroleum ether

출처 및 근거

ORD 기록: ord-475bb957a2534f33886ec0b0ee0f4e0c
출처 데이터셋: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US04528382

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