Ethanol → N-(4-aminobenzenesulphonyl)iminodithiocarbonic acid dimethyl ester

HRID 65951Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].[C:14](=[S:16])=[S:15].[CH3:17]I.[CH2:19]([OH:21])C>>[CH3:17][S:15](=[N:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)(=[O:9])=[O:10])[C:14](=[S:16])[O:21][CH3:19]

Participants

Reactant 5

HCID 702Ethanol

HCID 5333Sulfanilamide

HCID 6328Methyl iodide

HCID 6348Carbon Disulfide

HCID 14798Sodium Hydroxide

Product 1

HCID 86733738N-(4-aminobenzenesulphonyl)iminodithiocarbonic acid dimethyl ester

Procedure

The reaction of 4-aminobenzenesulphonamide (17.2.g.) with sodium hydroxide, carbon disulphide and methyl iodide by the method described in Example 8, afforded N-(4-aminobenzenesulphonyl)iminodithiocarbonic acid dimethyl ester (9.4 g.), m.p. 202°-204° (from ethanol).

Sources & evidence

ORD record: ord-b8846f8338ab45e0a8529ed4f8dfab22
Source dataset: uspto-grants-1978_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04129657

Reaction notes

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