tert-Butyldimethylsilyl chloride → 2-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 1694824Notes

Reaction equation

HRID 1694824 reaction equation
[CH3:1][N:2]([CH3:11])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)(=[O:5])=[O:4].C([Li])CCC.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>O1CCCC1>[CH3:1][N:2]([CH3:11])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 395751N,N-Dimethyl-1H-imidazole-1-sulfonamideHCID 178418339Butyllithium

Product 1

HCID 64202092-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared in analogy to Example 44(a) from 1-(dimethylsulfamoyl)-imidazole, butyl lithium and tert-butyldimethylsilyl chloride in tetrahydrofuran to afford 2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide, then treatment of this with butyl lithium and 2,6-diethyl-4-phenoxy-benzaldehyde in tetrahydrofuran. White crystalline solid. MS (ISP): 544.5 ([M+H]+).

Sources & evidence

ORD record
ord-f17096ec7ed54732b259b46a2e9d552d
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Reaction notes

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