1,4-Dibromobutane → 5-Chloro-3-methyl-6-(pyrrolidin-1-yl)-benzofuran

HRID 637686노트

반응식

HRID 637686 반응식
[NH2:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]2[C:6]([CH3:9])=[CH:7][O:8][C:4]=2[CH:3]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17]Br.C(N(C(C)C)C(C)C)C>C(O)C>[Cl:12][C:11]1[C:2]([N:1]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:3][C:4]2[O:8][CH:7]=[C:6]([CH3:9])[C:5]=2[CH:10]=1

참가 물질

5

반응물 3

HCID 80561,4-DibromobutaneHCID 81531DiisopropylethylamineHCID 202556476-Amino-5-chloro-3-methylbenzofuran

생성물 1

HCID 202556495-Chloro-3-methyl-6-(pyrrolidin-1-yl)-benzofuran

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 9.1 g (50 mmole) of 6-amino-5-chloro-3-methylbenzofuran, 11.8 ml (0.1 mole) of 1,4-dibromobutane, 17.1 ml (0.1 mole) of N-ethyldiisopropylamine and 60 ml of ethanol is boiled under reflux for 24 hours and then concentrated by evaporation in vacuo. The residue is partitioned between methylene chloride and saturated sodium bicarbonate solution. The crude product obtained after drying and concentration by evaporation of the methylene chloride is chromatographed with petroleum ether/ether over silica gel. Subsequent distillation in a bulb tube (150°/10-1 torr) yields 5-chloro-3-methyl-6-(pyrrolidin-1-yl)-benzofuran having a melting point of 50°-52°.

후처리

  1. temperatureunder reflux for 24 hours
  2. concentrationconcentrated by evaporation in vacuo
  3. customThe residue is partitioned between methylene chloride and saturated sodium bicarbonate solution
  4. customThe crude product obtained
  5. customafter drying
  6. concentrationconcentration
  7. customby evaporation of the methylene chloride
  8. customis chromatographed with petroleum ether/ether over silica gel
  9. distillationSubsequent distillation in a bulb tube (150°/10-1 torr)

출처 및 근거

ORD 기록
ord-220f058344494205a4cde4decc2594ca
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04558043

반응 노트

불러오는 중…