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

HRID 507001ノート

反応式

HRID 507001 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3a76c2ac45a3465382591ed0185de999
出典データセット
uspto-grants-2010_08
特許番号
US07786115B2

反応ノート

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