Allyl bromide → 3-(allylamino)-N-cyclopropyl-4-methylbenzamide

HRID 507001노트

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HRID 507001 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23]>C(#N)C>[CH2:23]([NH:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:5]([NH:7][CH:8]1[CH2:9][CH2:10]1)=[O:6])[CH:22]=[CH2:21]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 119838543-amino-N-cyclopropyl-4-methylbenzamide

생성물 1

HCID 670185693-(allylamino)-N-cyclopropyl-4-methylbenzamide

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

반응 조건

온도
80 °C

실험 절차

To a solution of 3-amino-N-cyclopropyl-4-methylbenzamide (2 g) in acetonitrile (10 ml) was added with potassium carbonate (2.6 g). The mixture was heated to 80° C. and a solution of allyl bromide (1.1 ml) in acetonitrile (6 ml) was added dropwise and heating was continued for 17 hours. The insoluble material was removed by filtration. The filtrate was concentrated and the residue was recrystallised from 50% ethyl acetate/hexane. The mother liquors was concentrated and by column chromatography on a silica column eluting using a gradient of iso-hexane to 50% ethyl acetate/iso-hexane to yield 3-(allylamino)-N-cyclopropyl-4-methylbenzamide as a colourless oil which solidified to a white solid (688 mg); NMR Spectrum: (DMSOd6) 0.53 m, 2H), 0.78 (m, 2H), 2.10 (s, 3H), 2.81 (m, 1H), 3.67 (s, 1H), 3.81 (d, 2H), 5.13 (d, 1H), 5.23 (d, 1H), 5.93 (m, 1H), 6.11 (s, 1H), 6.83 (d, 1H), 6.98 (m, 2H); Mass Spectrum: M+H+ 231.

후처리

  1. temperatureheating
  2. customThe insoluble material was removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customthe residue was recrystallised from 50% ethyl acetate/hexane
  5. concentrationThe mother liquors was concentrated and by column chromatography on a silica column
  6. washeluting

출처 및 근거

ORD 기록
ord-3a76c2ac45a3465382591ed0185de999
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786115B2

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