Dimethylformamide → Bis{4-[(phenylmethyl)oxy]phenyl}disulfide

HRID 130431

반응식

HRID 130431 반응식
[C:1](=[O:4])([O-])[O-].[K+].[K+].[C:7]1(O)[CH:12]=[CH:11][C:10]([S:13][S:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1.CN(C)C=O.[CH2:28](Cl)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CO.O>[C:29]1([CH2:28][O:21][C:18]2[CH:19]=[CH:20][C:15]([S:14][S:13][C:10]3[CH:11]=[CH:12][C:7]([O:4][CH2:1][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[CH:8][CH:9]=3)=[CH:16][CH:17]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 2806654-[(4-Hydroxyphenyl)disulfanyl]phenol

생성물 1

HCID 54075991Bis{4-[(phenylmethyl)oxy]phenyl}disulfide

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

To solid potassium carbonate (11.59 g, 83.89 mmol) was added 4,4′-dithiodiphenol (7.00 g, 27.96 mmol), as a solid under argon, followed by N,N-dimethylformamide (130 ml). The stirred suspension was then heated to 80° C. over 2.25 h. Benzyl chloride (7.24 ml, 62.91 mmol) was then added over 2-3 minutes and the mixture stirred at 80° C. overnight. The mixture was then allowed to cool slowly to room temperature over the weekend. The resulting mixture was then poured into water (800 ml) and extracted with dichloromethane (3×250 ml). The organic extracts were combined and dried over sodium sulfate, filtered and evaporated to give a pale yellow solid which was tritureated with hot methanol (80 ml) which was allowed to cool slowly overnight to afford the title compound (D47). 1H-NMR (CDCl3) d 7.43-7.33 (14H, m), 6.90 (4H, dd, J 6.8 Hz, 2.0 Hz), 5.05 (4H, s).

후처리

  1. temperatureto cool slowly to room temperature over the weekend
  2. extractionextracted with dichloromethane (3×250 ml)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a pale yellow solid which
  7. temperatureto cool slowly overnight

출처 및 근거

ORD 기록
ord-c915a03f01c64507a69c749c000acad5
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381728B2

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