Imidazole → N,N-Dimethyl-1H-imidazole-1-sulfonamide

HRID 1708505Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:6][N:7]([CH3:12])[S:8](Cl)(=[O:10])=[O:9]>>[CH3:6][N:7]([CH3:12])[S:8]([N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)(=[O:10])=[O:9]

Participants

Reactant 2

HCID 795Imidazole

HCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 395751N,N-Dimethyl-1H-imidazole-1-sulfonamide

Procedure

Imidazole was treated with dimethyl amino sulfonyl chloride providing 1-(dimethylaminosulfonyl)-imidazole, which was subsequently treated with n-butyl lithium and t-butyldimethylsilyl chloride to afford 1-(dimethylaminosulfonyl)-2-(t-butyldimethylsilyl)-imidazol e. This material was treated with n-butyllithium and tri-n-butyltin chloride to afford the target compound.

Sources & evidence

ORD record: ord-ad631ce524fd45f4aa207552e089d1ca
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05359051

Reaction notes

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