Tetrabutylammonium Fluoride → N-benzenesulfonyl-4-ethinylbenzoic acid amide

HRID 55302Notes

Reaction equation

HRID 55302 reaction equation
[C:1]1([S:7]([NH:10][C:11](=[O:24])[C:12]2[CH:17]=[CH:16][C:15]([C:18]#[C:19][Si](C)(C)C)=[CH:14][CH:13]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]1([S:7]([NH:10][C:11](=[O:24])[C:12]2[CH:13]=[CH:14][C:15]([C:18]#[CH:19])=[CH:16][CH:17]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53860484N-benzenesulfonyl-4-(2-trimethylsilylethinyl)-benzoic acid amide

Product 1

HCID 54259246N-benzenesulfonyl-4-ethinylbenzoic acid amideYield 121.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under the conditions of example 21 C, a solution of 3.1 g of N-benzenesulfonyl-4-(2-trimethylsilylethinyl)-benzoic acid amide in 200 ml of tetrahydrofuran is reacted with 9.5 ml of a 1-molar solution of tetrabutylammonium fluoride in tetrahydrofuran and worked up. 3 g of N-benzenesulfonyl-4-ethinylbenzoic acid amide is obtained as crude product.

Sources & evidence

ORD record
ord-3b343080f14e43bba26e9ab2084b6e19
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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