Nicotinic Acid → Succinimidyl Nicotinate

HRID 466299

反応式

HRID 466299 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 recrystallized 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 recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-b01c7bc7847941a58082d67743a4a844
出典データセット
uspto-grants-1992_10
特許番号
US05155227

関連ノート

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