Sodium hydride → HCID 19825143, compound

HRID 727823Notes

Reaction equation

HRID 727823 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[C:8]([C:10]1[NH:11][CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])[N:14]=1)#[N:9].[H-].[Na+]>>[C:8]([C:10]1[N:11]([S:3](=[O:5])(=[O:4])[N:2]([CH3:7])[CH3:1])[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])[N:14]=1)#[N:9]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 178510564HCID 178510564, compound

Product 1

HCID 19825143HCID 19825143, compound

Procedure

Dimethylsulphamoyl chloride (0.54 ml) was added to a mixture of 2-cyano-4-(2-nitrophenyl)-1H-imidazole (0.865 g) and sodium hydride (150 mg of 80% in oil). The mixture was heated under reflux for one hour and then poured into ice/water and extracted with ethyl acetate. The extract was washed with brine, dried and evaporated. The residual oil slowly solidified and was washed with ether and filtered to give 2-cyano-1-(dimethylsulphamoyl)4-(2-nitrophenyl)imidazole, m.p. 111°-4°. (Compound 4)

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for one hour
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. customdried
  6. customevaporated
  7. washwas washed with ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-98dc8a99ed0840c7b3da26dec16c61ce
Source dataset
uspto-grants-1991_09
Patent number
US05045557

Reaction notes

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