Hydrochloric Acid → 4-Ethynylbenzenesulfonamide

HRID 854934Notes

Reaction equation

HRID 854934 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCOC(C)=O.Cl>C1COCC1>[C:6]([C:7]1[CH:8]=[CH:9][C:10]([S:13]([NH2:16])(=[O:14])=[O:15])=[CH:11][CH:12]=1)#[CH:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl Acetate2×HCID 2724141Tetrabutylammonium FluorideHCID 695174394-((Trimethylsilyl)ethynyl)benzenesulfonamide

Product 1

HCID 444572214-EthynylbenzenesulfonamideYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[(trimethylsilyl)ethynyl]benzenesulfonamide prepared as in Step 1 (1.69 g, 3.13 mmole) in anhydrous THF under a N2 atmosphere was added TBAF (10 mL-1.0 M in THF, 10 mmole) and the resulting mixture was stirred at room temperature. When silica TLC (1:1 hexanes:EtOAc) indicated the reaction was complete, 10% HCl and EtOAc were added. The EtOAc layer was separated, washed twice with H2O, aqueous NH4Cl, dried over Na2SO4 and concentrated in vacuo to give 0.748 g (62% yield) of the product: ESHRMS m/z 199.0506 (M+NH4, C8H7NO2SNH4, Calc'd 199.0541).

Workup

  1. customThe EtOAc layer was separated
  2. washwashed twice with H2O, aqueous NH4Cl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca0b56da34bc4fb8833116bfbc1b1a45
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

Loading…