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

HRID 1449390노트

반응식

HRID 1449390 반응식
[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]

참가 물질

4

반응물 2

HCID 69828CyclopropylamineHCID 14959106trans 3-Bromocinnamoyl chloride

생성물 1

HCID 8220093-(3-bromophenyl)-N-cyclopropylacrylamide수율 90.7%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e149e2f0c44b4b1eb9cb638015eb0fed
출처 데이터셋
uspto-grants-1980_02
특허 번호
US04190674

반응 노트

불러오는 중…