Sodium hydride → HCID 67561440, compound

HRID 1601150Notes

Reaction equation

HRID 1601150 reaction equation
[CH2:1]([C:5]1[NH:6][CH:7]=[C:8]([S:10][CH3:11])[N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]([S:28]([N:31]=[CH:32][N:33]([CH3:35])[CH3:34])(=[O:30])=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:18][CH:17]=1>C1COCC1.O>[CH2:1]([C:5]1[N:6]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[C:23]([S:28]([N:31]=[CH:32][N:33]([CH3:34])[CH3:35])(=[O:30])=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:20][CH:21]=2)[CH:7]=[C:8]([S:10][CH3:11])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 541617064'-Bromomethylbiphenyl-2-sulfonic acid dimethylaminomethylenamideHCID 178441882HCID 178441882, compound

Product 1

HCID 67561440HCID 67561440, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

5 g of 2-butyl 4-(methylthio)1H-imidazole is dissolved in 120 cm3 of THF. 1.55 g of 50% sodium hydride dispersed in oil is then added slowly to the orange-coloured solution obtained. The temperature is increased to 25° C. The reaction medium is agitated for 30 minutes at this temperature then 14 g of 4'-bromomethyl N-[(dimethylamino)methylene](1,1'-biphenyl)2-sulphonamide is introduced. Agitation is carried out at ambient temperature until evolution is complete, that is for about 3 hours. The resultant product is taken up in water, extraction is carried out with ethyl acetate, followed by separation by chromatography on silica, eluting with ethyl acetate then impasting in iso ether, filtration and drying. In this way 9.35 g of the expected product (colourless crystals) is obtained. M.p.=148° C.

Workup

  1. additionis then added slowly to the orange-coloured solution
  2. customobtained
  3. customis carried out at ambient temperature until evolution
  4. waitthat is for about 3 hours
  5. extractionextraction
  6. customfollowed by separation by chromatography on silica
  7. washeluting with ethyl acetate
  8. filtrationthen impasting in iso ether, filtration
  9. customdrying

Sources & evidence

ORD record
ord-1baaab39228447aa844a3b07f68a9a16
Source dataset
uspto-grants-1999_11
Patent number
US05977155

Reaction notes

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