Cyclopropylamine → 3-(3-bromophenyl)-N-cyclopropylacrylamide

HRID 1449390ノート

反応式

HRID 1449390 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7](Cl)=[O:8].[CH:13]1([NH2:16])[CH2:15][CH2:14]1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]([NH:16][CH:13]1[CH2:15][CH2:14]1)=[O:8]

参加物

4

反応物 2

HCID 69828CyclopropylamineHCID 14959106trans 3-Bromocinnamoyl chloride

生成物 1

HCID 8220093-(3-bromophenyl)-N-cyclopropylacrylamide収率 90.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

A solution of trans 3-bromocinnamoyl chloride (12.2 g) in dry toluene (150 ml) was added dropwise (rapidly) with rapid stirring to a solution of cyclopropylamine (6.3 g) in dry toluene (150 ml). The reaction mixture was stirred at room temperature for 2 hours, then at 30°-35° C. for an additional hour; and the solvent and excess amine were removed under reduced pressure. The residue was triturated with water to remove cyclopropylamine hydrochloride. The product was filtered, washed with dilute hydrochloric acid and then with water. It was then recrystallized from ethanol:water (1:10) to give white crystalline trans 3-bromo-N-cyclopropylcinnamamide (12 g), m.p. 110°-111° C. Elemental analysis, NMR and 1R data were all consistent with the assigned structure. TLC gave one spot run on silica gel with 5:1 and with 3:1 hexane:ethanol.

後処理

  1. waitat 30°-35° C. for an additional hour
  2. customand the solvent and excess amine were removed under reduced pressure
  3. customThe residue was triturated with water
  4. customto remove cyclopropylamine hydrochloride
  5. filtrationThe product was filtered
  6. washwashed with dilute hydrochloric acid
  7. customIt was then recrystallized from ethanol:water (1:10)

出典と根拠

ORDレコード
ord-e149e2f0c44b4b1eb9cb638015eb0fed
出典データセット
uspto-grants-1980_02
特許番号
US04190674

反応ノート

読み込み中…