Pyridine → N-cyclopropanecarbonyl-5-bromovaleramide

HRID 1075842

反応式

HRID 1075842 の反応式
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[CH:9]1([C:12]([NH2:14])=[O:13])[CH2:11][CH2:10]1.N1C=CC=CC=1>COCCOC>[CH:9]1([C:12]([NH:14][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][Br:1])=[O:13])[CH2:11][CH2:10]1

参加物

5

反応物 3

HCID 1049PyridineHCID 80376CyclopropanecarboxamideHCID 5211735-Bromovaleryl chloride

生成物 1

HCID 21540959N-cyclopropanecarbonyl-5-bromovaleramide収率 40%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

A solution of 7.96 g. of 5-bromovaleric acid chloride, 3.40 g. of cyclopropanecarboxamide, 3.16 g. of pyridine, and 20 ml. of 1,2-dimethoxyethane was heated to reflux under nitrogen for 1.5 hours, then was concentrated by rotary evaporation. The resultant semi-solid was triturated with methylene chloride (2X). The combined methylene chloride layers were washed with saturated brine, were dried (anhydrous magnesium sulfate), were treated with activated charcoal, and were filtered. The filtrate was concentrated on a steam-bath with addition of hexane until crystallization started. Thus, 3.98 g. (40% yield) of white, crystalline N-cyclopropanecarbonyl-5-bromovaleramide was obtained melting at 114°-115°C.

後処理

  1. temperatureto reflux under nitrogen for 1.5 hours
  2. concentrationwas concentrated by rotary evaporation
  3. customThe resultant semi-solid was triturated with methylene chloride (2X)
  4. washThe combined methylene chloride layers were washed with saturated brine
  5. dry with materialwere dried (anhydrous magnesium sulfate)
  6. additionwere treated with activated charcoal
  7. filtrationwere filtered
  8. concentrationThe filtrate was concentrated on a steam-bath with addition of hexane until crystallization

出典と根拠

ORDレコード
ord-3223fb83941c4d6d8d19abeb00875317
出典データセット
uspto-grants-1976_05
特許番号
US03954741

関連ノート

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