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Sodium Iodide → 4-[3-[Ethyl[3-(phenylthio) propyl]amino]-2-hydroxypropoxy]-benzonitrile

HRID 1087113
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HRID 1087113 반응식
[CH2:1]([NH:3][CH2:4][CH:5]([OH:16])[CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)[CH3:2].Cl[CH2:18][CH2:19][CH2:20][S:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH2:1]([N:3]([CH2:18][CH2:19][CH2:20][S:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:4][CH:5]([OH:16])[CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=1)[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2696063-Chloropropyl phenyl sulfideHCID 150668414-[3-(Ethylamino)-2-hydroxypropoxy]-benzonitrile

생성물 1

HCID 151588134-[3-[Ethyl[3-(phenylthio) propyl]amino]-2-hydroxypropoxy]-benzonitrile

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

5.0 g of 4-[3-(ethylamino)-2-hydroxypropoxy]-benzonitrile and 4.0 g of 1-chloro-3-(phenylthio) propane was dissolved in 70 ml of acetonitrile and mixed with 6.4 g potassium carbonate and 8.0 g of sodium iodide. The mixture was refluxed over night, filtrated, evaporated and the residue was dissolved in 2 M hydrochloric acid. This acidic waterlayer was washed with two portions of diethylether, alkalized with 10 M sodium hydroxide and extracted with three portions of dichlorometane. The combined layers of dichloromethane were dried over sodium sulphate and evaporated. The oily residue was purified by column chromatography on silica gel. Yield: 2.1 g of the title compound.

후처리

  1. temperatureThe mixture was refluxed over night
  2. filtrationfiltrated
  3. customevaporated
  4. dissolutionthe residue was dissolved in 2 M hydrochloric acid
  5. washThis acidic waterlayer was washed with two portions of diethylether
  6. extractionextracted with three portions of dichlorometane
  7. dry with materialThe combined layers of dichloromethane were dried over sodium sulphate
  8. customevaporated
  9. customThe oily residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-bf82bb9fe8d34ba0a569d0bd55d8b34a
출처 데이터셋
uspto-grants-1991_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05034411

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