Sodium hydride → HCID 67561440, compound

HRID 2393567Notes

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

Conditions

Temperature: 25 °C

Procedure

5 g de 2-butyl 4-(methylthio) 1H-imidazole is dissolved in 120 cm3 of THF. Then 1.55 g of sodium hydride at 50% dispersion in oil is added slowly to the orange-coloured solution obtained. The temperature increases to 25° C. Agitation is carried out 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 ends, i.e. for approximately 3 hours, followed by taking up in water, extracting with ethyl acetate, separating by chromatography on silica eluting with ethyl acetate then impasting in iso ether, filtering and drying. In this way 9.35 g of expected product (colourless crystals) is obtained.

Workup

customobtained
waitAgitation is carried out at ambient temperature until evolution ends, i.e. for approximately 3 hours
extractionextracting with ethyl acetate
customseparating by chromatography on silica eluting with ethyl acetate
filtrationfiltering
customdrying

Sources & evidence

ORD record: ord-6b7de749a960459891e492e87a192d55
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05807878

Reaction notes

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