2-Naphthalenethiol → N-[6-(2-naphthylthio)hexyl]phthalimide

HRID 54915

반응식

HRID 54915 반응식
C(=O)([O-])[O-].[K+].[K+].[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[SH:17].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Cl.[C:26]1(=[O:36])[NH:30][C:29](=[O:31])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12.[K]>CN(C)C=O.O>[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[S:17][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:30]1[C:29](=[O:31])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]2[C:26]1=[O:36]

참가 물질

7

반응물 4

HCID 70582-NaphthalenethiolHCID 11430Potassium CarbonateHCID 805161-Bromo-6-chlorohexaneHCID 24194345Phthalimide potassium salt

생성물 1

HCID 19956979N-[6-(2-naphthylthio)hexyl]phthalimide수율 95.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Potassium carbonate (8.29 g) was added to a solution of 2-naphthalenethiol (8.01 g) and 1-bromo-6-chlorohexane (9.98 g) in N,N-dimethylformamide (65 ml). The mixture was stirred at room temperature for 3 hours. Then potassium phthalimide (9.26 g) was added to the mixture, and the resulting mixture was stirred at 100° C. for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), and the solvent was distilled off under reduced pressure to obtain N-[6-(2-naphthylthio)hexyl]phthalimide (18.56 g, 95.3%), which was then recrystallized from ethyl acetate-hexane. Colorless plate, mp: 109°-110° C.

후처리

  1. stirringthe resulting mixture was stirred at 100° C. for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-04dc9cd25c024ef0ba055288c5c663ad
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624917

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