Benzene → 2-(Phenylthio)-5-(trifluoromethyl)benzonitrile

HRID 435714노트

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HRID 435714 반응식
N[C:2]1[CH:3]=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:5]=[CH:6][C:7]=1SC1C=CC=CC=1.[CH3:19][S:20](O)(=O)=O.[N:24]([O-])=O.[Na+].[CH:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O>[C:28]1([S:20][C:19]2[CH:6]=[CH:5][C:4]([C:15]([F:18])([F:17])[F:16])=[CH:3][C:2]=2[C:7]#[N:24])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

6

반응물 4

HCID 241BenzeneHCID 6395Methanesulfonic AcidHCID 125903632-(Phenylsulfanyl)-5-(trifluoromethyl)anilineHCID 23668193Sodium Nitrite

생성물 1

HCID 14895212-(Phenylthio)-5-(trifluoromethyl)benzonitrile

시약·촉매·용매 1

HCID 962Water용매2회

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온도
0 °C

실험 절차

36 g of 3-amino-4-(phenylthio)-benzotrifluoride, 70 ml of water and 21 ml of methanesulphonic acid are heated to 90° C, stirred at this temperature for 20 minutes and subsequently cooled to 0° C. The suspension obtained is treated dropwise over a period of 15 minutes at 0° C with a solution of 9.25 g of sodium nitrite in 33 ml of water, care being taken to ensure that the temperature does not rise above 10° C. The mixture is stirred for about 1 hour at 0° C, filtered and added over a period of about 45 minutes to a suspension of copper cyanide pre-warmed to 100° C (prepared by the addition of 33.75 g of copper sulphate to 37 g of potassium cyanide in 165 ml of water). The dark solution obtained is stirred at 100° C for 1 hour, cooled, treated with 350 ml of benzene and stirred overnight. The mixture is filtered through diatomaceous earth and the filter cake washed with benzene. The organic phase is washed twice with 150 ml of saturated sodium chloride solution each time, dried over sodium sulphate, filtered and evaporated. There is obtained 2-(phenylthio)-5-trifluoromethyl-benzonitrile as a dark oil.

후처리

  1. customThe suspension obtained
  2. customdoes not rise above 10° C
  3. stirringThe mixture is stirred for about 1 hour at 0° C
  4. filtrationfiltered
  5. additionadded over a period of about 45 minutes to a suspension of copper cyanide
  6. temperaturepre-warmed to 100° C (
  7. customprepared by the addition of 33.75 g of copper sulphate to 37 g of potassium cyanide in 165 ml of water)
  8. customThe dark solution obtained
  9. stirringis stirred at 100° C for 1 hour
  10. temperaturecooled
  11. stirringstirred overnight
  12. filtrationThe mixture is filtered through diatomaceous earth
  13. washthe filter cake washed with benzene
  14. washThe organic phase is washed twice with 150 ml of saturated sodium chloride solution each time
  15. dry with materialdried over sodium sulphate
  16. filtrationfiltered
  17. customevaporated

출처 및 근거

ORD 기록
ord-661c4b618fc446978c709f402ca4715a
출처 데이터셋
uspto-grants-1977_02
특허 번호
US04006144

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