Sulfuric Acid → 2,6-Dichloro-4-methylbenzamide

반응식

[Cl:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[C:4]#[N:5].S(=O)(=O)(O)[OH:13]>>[Cl:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[C:4]([NH2:5])=[O:13]

참가 물질

반응물 2

HCID 1118Sulfuric Acid

HCID 136496782,6-Dichloro-4-methylbenzonitrile

생성물 1

HCID 136496812,6-Dichloro-4-methylbenzamide수율 59%

실험 절차

To stirred, cooled concentrated sulfuric acid (40 ml) was added in portions 2,6-dichloro-4-methylbenzonitrile (13.2 g, 71.0 mmol). The mixture was heated on a steam bath for 3 hours with occasional shaking, cooled, poured into ice-water, and extracted twice with dichloromethane. The combined extracts were washed with brine, dried over anhydrous magnesium sulfate, and evaporated under vacuum. The residue was chromatographed on a column of silica gel (390 g) eluted with 4:1 (v/v) dichloromethane-diethyl ether to provide 8.6 g (59%) of 2,6-dichloro-4-methylbenzamide, m.p. 101°-107° C.

후처리

temperatureThe mixture was heated on a steam bath for 3 hours with occasional shaking
temperaturecooled
extractionextracted twice with dichloromethane
washThe combined extracts were washed with brine
dry with materialdried over anhydrous magnesium sulfate
customevaporated under vacuum
customThe residue was chromatographed on a column of silica gel (390 g)
washeluted with 4:1 (v/v) dichloromethane-diethyl ether

출처 및 근거

ORD 기록: ord-86059a1560274fa6b6651c7a841f8c25
출처 데이터셋: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US04590201

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