Water → HCID 18416681, compound

HRID 990800Notes

Reaction equation

HRID 990800 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)=[C:2]=[S:3].[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].[H-].[Na+].O>C1COCC1>[N:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])(=[O:11])=[O:12])=[CH:8][CH:9]=1)=[C:2]=[S:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 5213594-Isothiocyanatobenzenesulfonamide

Product 1

HCID 18416681HCID 18416681, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Isothiocyanato-benzenesulfonamide (750 mg, 3.5 mmol), and tert-butyldimethylsilyl chloride (528 mg, 3.5 mmol) stirred in dry THF (20 mL) at 0° C. Sodium hydride (210 mg, 60% in mineral oil, 5.25 mmol) was added, and the reaction stirred for 1 h before it was poured over H2O (50 mL) and extracted with ether (2×50 mL). Organics were washed with brine (25 mL), dried (Na2SO4), and concentrated in vacuo. Purification by silica gel chromatography gave 920 mg (80%) of 4-isothiocyanato-N-(TBDMS)-benzenesulfonamide as a white solid. 1H NMR (300 MHz, CDCl3) δ7.86 (d, 2H, J=6.9 Hz), 7.31 (d, 2 H, J=6.9 Hz), 4.40 (s, 1H), 0.90 (s, 9H), 0.22 (s, 6H). Anal. (C13H20N2O2S2Si) C, H, N, S. Calculated C=47.53; H=6.14; N=8.53; S=19.52; found C=47.47; H=6.25; N=8.46; S=19.49.

Workup

  1. extractionextracted with ether (2×50 mL)
  2. washOrganics were washed with brine (25 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-f8c212bfaddc46dda8f7969886a01857
Source dataset
uspto-grants-2002_10
Patent number
US06462069B2

Reaction notes

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