Dimethylformamide → N-(N-[Bicyclo[2.2.1]hept-2-en-5-ylmethyl]carbamoyl)-2-phenylethenesulfonamide

HRID 461465

반응식

HRID 461465 반응식
[C:1]1([CH:7]=[CH:8][S:9]([NH2:12])(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(N(C2C=CC=CC=2)[C:20]([NH:22][CH2:23][CH:24]2[CH2:29][CH:28]3[CH2:30][CH:25]2[CH:26]=[CH:27]3)=[O:21])C=CC=CC=1.CN(C)C=O.[H-].[Na+]>CCOCC>[CH:28]12[CH2:30][CH:25]([CH:24]([CH2:23][NH:22][C:20]([NH:12][S:9]([CH:8]=[CH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:10])=[O:11])=[O:21])[CH2:29]1)[CH:26]=[CH:27]2

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 2575012-PhenylethenesulfonamideHCID 12282081N'-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)-N,N-diphenylurea

생성물 1

HCID 54231290N-(N-[Bicyclo[2.2.1]hept-2-en-5-ylmethyl]carbamoyl)-2-phenylethenesulfonamide

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of 1.8 g. of 2-phenylethenesulfonamide and 4.8 g. of 1,1-diphenyl-3-(bicyclo[2.2.1]hept-2-en-5-ylmethyl)urea in 20 ml. of N,N-dimethylformamide, is added, with stirring 0.64 g. of a 56.6% dispersion of sodium hydride in mineral oil. The mixture is stirred at ambient temperature overnight, during which time a heavy precipitate forms. To the reaction mixture is then added 200 ml. of ether. After stirring for 15 minutes, the precipitate is filtered off. It is dissolved in 50 ml. of water, and then the crude product is precipitated by acidification usng concentrated hydrochloric acid. It is filtered off and recrystallized from aqueous acetone. The yield is 1.9 g. (56%) of a solid, m.p. 161°-163.5° C.

후처리

  1. stirringThe mixture is stirred at ambient temperature overnight, during which time a heavy precipitate forms
  2. additionTo the reaction mixture is then added 200 ml
  3. stirringAfter stirring for 15 minutes
  4. filtrationthe precipitate is filtered off
  5. dissolutionIt is dissolved in 50 ml
  6. customof water, and then the crude product is precipitated by acidification usng concentrated hydrochloric acid
  7. filtrationIt is filtered off
  8. customrecrystallized from aqueous acetone

출처 및 근거

ORD 기록
ord-0f04b68366f946ca8929ad0918755bef
출처 데이터셋
uspto-grants-1977_12
특허 번호
US04062960

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