Nicotinic Acid → Succinimidyl Nicotinate

HRID 4578

反応式

HRID 4578 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.CCOCC>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

6

反応物 4

HCID 938Nicotinic AcidHCID 3283Diethyl EtherHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

生成物 1

HCID 870586Succinimidyl Nicotinate収率 72%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

Nicotinic acid (4.025 g, 0.0327 mol) and N-hydroxysuccinimide (3.763 g, 0.0327 mol) were dissolved in 130 ml of dioxane. Dicyclohexylcarbodiimide (6.75 g, 0.032 mol) in 20 ml of dioxane was added. The reaction mixture was then stirred at room temperature for 3 hours. The dicyclohexylurea which precipitated was removed by filtration and the solvent was removed by rotary evaporation. The crude product was recrystallized from ethyl acetate to give light yellow crystals which were then waashed with anhydrous ether. The product, obtained in 72% yield (5.2 g) and melting at 129°-131° C., has the formula: ##STR40##

後処理

  1. customThe dicyclohexylurea which precipitated
  2. customwas removed by filtration
  3. customthe solvent was removed by rotary evaporation
  4. customThe crude product was recrystallized from ethyl acetate
  5. customto give light yellow crystals which
  6. customThe product, obtained in 72% yield (5.2 g) and melting at 129°-131° C.

出典と根拠

ORDレコード
ord-c4b9f4b95d474b5a9a51663bf3ff7ff1
出典データセット
uspto-grants-1988_02
特許番号
US04727079

関連ノート

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