HCID 14984036, compound → HCID 14984037, compound

HRID 864732Notes

Reaction equation

HRID 864732 reaction equation
N[S:2]([C:5]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]([Si:20]([CH3:23])([CH3:22])[CH3:21])[CH3:19])[C:6]=1[C:7]([N:9](CC)CC)=[O:8])(=[O:4])=[O:3]>C(O)(=O)C>[CH3:21][Si:20]([CH3:23])([CH3:22])[CH:18]([C:14]1[CH:15]=[CH:16][CH:17]=[C:5]2[C:6]=1[C:7](=[O:8])[NH:9][S:2]2(=[O:4])=[O:3])[CH3:19]

Participants

3

Reactant 1

HCID 14984036HCID 14984036, compound

Product 1

HCID 14984037HCID 14984037, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of sec-BuLi (0.97M, 5.10 mL, 4.96 mmol) and TMEDA (0.75 mL, 4.96 mmol) in THF at -78° C. was added the amide (1.25 g, 4.50 mmol) in THF. Excess SO2 in THF was added quickly at -78° C. then warmed to room temperature. The THF was removed in vacuo and the residue treated at 0° C. with two equivalents of a 1:1 solution of sodium hydroxide (0.36 g, 9.0 mmol) and hydroxylamine-O-sulfonic acid (1.0 g, 9.0 mmol) in H2O. The reaction was stirred at room temperature for 4 hrs, extracted with EtOAc, dried over MgSO4, concentrated and flash chromatographed on silica gel with 20% ethyl acetate/hexane to give 0.62 g (41%) of 2-aminosulfonyl-N,N-diethyl-6-[1-(trimethylsilyl)-ethyl]benzamide. The benzamide (0.95 g, 2.66 mol) was refluxed in glacial acetic acid (20 mL) for 18 hr, stripped to dryness, triturated with hot cyclohexane (30 mL) and a trace of EtOAc (3 mL), cooled with scratching and filtered. There was obtained 0.81 g (85%) of 4-[1-(trimethylsilyl)-ethyl]saccharin, mp 123°-125° C.

Workup

  1. customtriturated with hot cyclohexane (30 mL)
  2. temperaturea trace of EtOAc (3 mL), cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-b436d83e1eda44d4af8c90ea4f3effba
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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