Nicotinic Acid → Succinimidyl Nicotinate

HRID 466299

반응식

HRID 466299 반응식
[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

참가 물질

5

반응물 3

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

생성물 1

HCID 870586Succinimidyl Nicotinate수율 63.6%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b01c7bc7847941a58082d67743a4a844
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155227

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