Ammonia → N-(Trimethylsilyl)benzenesulfonamide

HRID 435194Notes

Reaction equation

HRID 435194 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[NH:3][Si](C)(C)C.[C:10]1([S:16](N)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.S1(C2C(=CC=CC=2)C(=O)N1)(=O)=O.N.OS(O)(=O)=O>C(OCC)(=O)C.O>[CH3:1][Si:2]([CH3:9])([CH3:8])[NH:3][S:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:18])=[O:17]

Participants

8

Reactant 5

HCID 222Ammonia2×HCID 1118Sulfuric AcidHCID 5143SaccharinHCID 7370BenzenesulfonamideHCID 13838Hexamethyldisilazane

Product 1

HCID 12271451N-(Trimethylsilyl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

15.6 ml of hexamethyldisilazane (75 mmoles) were added to a refluxing suspension of 15.72 g (0.1 mole) of benzenesulfonamide and 18 mg (0.1 mmole) of saccharin in 45 ml of ethyl acetate under nitrogen and the nitrogen was passed through water to determine the amount of ammonia evolved. By titrating with 1 N H2SO4, it was found that the calculated amount of ammonia was set free in 25 minutes and the residue of N-trimethylsilylbenzensulfonamide obtained after evaporating the volatile materials in vacuo melted at 62°-63° C.

Sources & evidence

ORD record
ord-724b127224144fe9a370dd271eec24ce
Source dataset
uspto-grants-1983_08
Patent number
US04400509

Reaction notes

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