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

HRID 54915

反応式

HRID 54915 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-04dc9cd25c024ef0ba055288c5c663ad
出典データセット
uspto-grants-1997_04
特許番号
US05624917

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