Aniline → Malonanilide

반응식

[C:1]1(=[O:6])O[C:3](=[O:4])[CH2:2]1.[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:1]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:6])[CH2:2][C:3]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

참가 물질

반응물 2

HCID 6115Aniline

HCID 10176090Malonic anhydride

생성물 1

HCID 69298Malonanilide수율 72%

실험 절차

To the cold solution of malonic anhydride, prepared as above, was added aniline (700 μl, 6 equivalents). The reaction mixture was allowed to warm to room temperature. It was then extracted with 5 ml saturated aqueous NaHCO3, and the aqueous extract was washed with 5 ml ether, acidified with H2SO4, and extracted with 3 4-ml portions of ether. The ether extracts were combined and dried over Na2SO4, and the ether was removed under reduced pressure, to leave a residue of malonanilide (mp 127°-130° C., 180 mg, 72% isolated yield, based on diketene).

후처리

extractionIt was then extracted with 5 ml saturated aqueous NaHCO3
extractionthe aqueous extract
washwas washed with 5 ml ether
extractionextracted with 3 4-ml portions of ether
dry with materialdried over Na2SO4
customthe ether was removed under reduced pressure

출처 및 근거

ORD 기록: ord-473b45e1376d481dac4b2702e1df3992
출처 데이터셋: uspto-grants-1981_02
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US04251447

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