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

HRID 461465

Reaction equation

HRID 461465 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0f04b68366f946ca8929ad0918755bef
Source dataset
uspto-grants-1977_12
Patent number
US04062960

Linked notes

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