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

HRID 2163686Notes

Reaction equation

HRID 2163686 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 using 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
  7. filtrationIt is filtered off
  8. customrecrystallized from aqueous acetone

Sources & evidence

ORD record
ord-433a9c28b0e34ae08a159161489d5569
Source dataset
uspto-grants-1979_01
Patent number
US04136180

Reaction notes

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