Nicotinic Acid → Succinimidyl Nicotinate

HRID 1089002

反応式

HRID 1089002 の反応式
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.O[N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]1=[O:17].C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[C:1]([O:9][N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]1=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

参加物

5

反応物 3

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

生成物 1

HCID 870586Succinimidyl Nicotinate収率 63.6%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

Nicotinic acid (12.3 g; 0.1 mole) and N-hydroxysuccinimide (11.5 g; 0.1 mole) are dissolved in 300 milliliters of hot dioxane. The mixture is cooled on an ice-bath and dicyclohexylcarbodiimide (20.6 g; 0.1 mole) in 30 milliliters of dioxane is added. The reaction mixture is stirred, with cooling, for approximately three hours, then refrigerated for at least 2 hours. The precipitated dicyclohexylurea is removed by filtration, the solution is condensed under vacuum, and the yellowish solids which precipitate are recrystalized from ethyl acetate. White crystals (14 g) of succinimidyl nicotinate are obtained (yield 63.6%). Structure of the product is confirmed by NMR.

後処理

  1. temperatureThe mixture is cooled on an ice-bath
  2. temperaturewith cooling, for approximately three hours
  3. waitrefrigerated for at least 2 hours
  4. customThe precipitated dicyclohexylurea is removed by filtration
  5. customcondensed under vacuum
  6. customthe yellowish solids which precipitate are recrystalized from ethyl acetate

出典と根拠

ORDレコード
ord-13b9133ff8f04259991f8518ac333f21
出典データセット
uspto-grants-1990_10
特許番号
US04963688

関連ノート

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