Phosphorus oxychloride → 3-Chlorocinnamonitrile

HRID 596782

반응식

[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7]([NH2:9])=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].P(Cl)(Cl)(Cl)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7]#[N:9]

참가 물질

반응물 3

HCID 24813Phosphorus oxychloride

HCID 656671Sodium Pyrosulfite

HCID 534396243-(3-Chlorophenyl)prop-2-enamide

생성물 1

HCID 3673163-Chlorocinnamonitrile수율 59.5%

실험 절차

m-Chlorocinnamamide (1.39 g.) was mixed with sodium metabisulphite (0.72 g.) and phosphoryl chloride (3 ml.). The mixture was heated on the steam-bath for 2.5 hr. and the phosphoryl chloride removed under reduced pressure. The residue was washed well with water, leaving slightly impure m-chlorocinnamonitrile (0.744 g., 59.5%). Recrystallisation from aqueous acetone gave m-chlorocinnamonitrile, m.p. 56°-57°, λmax. (EtOH) 226, 270 nm. ε 19000, 22500.

후처리

temperatureThe mixture was heated on the steam-bath for 2.5 hr
customand the phosphoryl chloride removed under reduced pressure
washThe residue was washed well with water

출처 및 근거

ORD 기록: ord-f89108d6e9ad4052b1035597098795e2
출처 데이터셋: uspto-grants-1977_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US04012377

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