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Phosphorus pentachloride → phenyl 2-methyl-N-phenyl-3-(phenylthio)thioacrylimidate

HRID 2061009
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인쇄 미리보기

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HRID 2061009 반응식
[CH3:1]/[C:2](=[CH:12]\[S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)/[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.P(Cl)(Cl)(Cl)(Cl)Cl.[Na].[C:27]1([SH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:1][C:2](=[CH:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([S:33][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[N:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 24819Phosphorus pentachlorideHCID 59498330(E)-2-methyl-N-phenyl-3-(phenylthio)-2-propenamideHCID 66586497Sodium benzenethiol

생성물 1

HCID 67543149phenyl 2-methyl-N-phenyl-3-(phenylthio)thioacrylimidate수율 36.9%

시약·촉매·용매 2

HCID 1140Toluene용매
HCID 6228
Dimethylformamide
용매

실험 절차

To a suspension of 0.8 g (3 mmol) of (E)-2-methyl-N-phenyl-3-(phenylthio)-2-propenamide in toluene (4 ml) was added 0.62 g (3 mmol) of phosphorus pentachloride and the mixture was stirred at room temperature for 4 hours. After concentration of the mixture under vacuum, the residue was dissolved in 35 ml of N,N-dimethylformamide [DMF] and then 793 mg (6 mmol) of a benzenethiol sodium salt was added portionwise under ice cooling. The mixture was stirred at room temperature for 2 hours. After dilution with tert-butyl methyl ether, the mixture was washed sequentially with water (three times) and saturated NaCl solution, dried over anhydrous MgSO4, and concentrated under vacuum. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1) to obtain 0.4 g of phenyl 2-methyl-N-phenyl-3-(phenylthio)-2-propenimidothioate (hereinafter referred to as the present compound 1).

후처리

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. washAfter dilution with tert-butyl methyl ether, the mixture was washed sequentially with water (three times) and saturated NaCl solution
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1)

출처 및 근거

ORD 기록
ord-5716523af6894a709898f1277332beef
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08278473B2

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