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

HRID 637686ノート

反応式

HRID 637686 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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°.

後処理

  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)

出典と根拠

ORDレコード
ord-220f058344494205a4cde4decc2594ca
出典データセット
uspto-grants-1985_12
特許番号
US04558043

反応ノート

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