Trimethylsilylacetylene → N-[3-(2-trimethylsilylethinyl)-phenyl]-1,1,1-trifluoromethanesulfonamide

HRID 55307Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18]>>[CH3:16][Si:17]([CH3:19])([CH3:18])[C:20]#[C:21][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 66111Trimethylsilylacetylene

HCID 19957504N-(3-iodophenyl)-1,1,1-trifluoromethanesulfonamide

Product 1

HCID 19957475N-[3-(2-trimethylsilylethinyl)-phenyl]-1,1,1-trifluoromethanesulfonamideYield 47.9%

Procedure

Under the conditions of example 5A, 6.2 g of N-(3-iodophenyl)-1,1,1-trifluoromethanesulfonamide is reacted with 2.07 g of trimethylsilylacetylene, worked up, and the crude product is chromatographed on silica gel with hexane/0-25% ethyl acetate. 2.72 g of N-[3-(2-trimethylsilylethinyl)-phenyl]-1,1,1-trifluoromethanesulfonamide is obtained as yellow oil.

Workup

customthe crude product is chromatographed on silica gel with hexane/0-25% ethyl acetate

Sources & evidence

ORD record: ord-fa77dcb9ba5a41bb927cf8647fb4b4ba
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624943

Reaction notes

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