Phosgene → N,N-dimethyl-2-chloro-5-isocyanatobenzenesulfonamide

HRID 375678Notes

Reaction equation

HRID 375678 reaction equation
[CH3:1][N:2]([CH3:14])[S:3]([C:6]1[CH:11]=[C:10]([NH2:12])[CH:9]=[CH:8][C:7]=1[Cl:13])(=[O:5])=[O:4].[C:15](Cl)(Cl)=[O:16]>C(OCC)(=O)C>[CH3:1][N:2]([CH3:14])[S:3]([C:6]1[CH:11]=[C:10]([N:12]=[C:15]=[O:16])[CH:9]=[CH:8][C:7]=1[Cl:13])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 36139385-amino-2-chloro-N,N-dimethylbenzene-1-sulfonamide

Product 1

HCID 18993674N,N-dimethyl-2-chloro-5-isocyanatobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

50 g of N,N-dimethyl-2-chloro-5-aminobenzenesulfonamide (Example A-3 above) was treated with an excess of phosgene in ethyl acetate as is generally described in "Organic Functional Group Preparations" by S. R. Sandler and W. Karo on pages 364-365 (Academic Press, N.Y., 1983) (preparation of organic isocyanates), which disclosure is herein incorporated by reference. 48 g of the title compound was isolated as a tan solid with a melting point of 82°-85° C.

Sources & evidence

ORD record
ord-f23b77868c744b8897d1fa549b920425
Source dataset
uspto-grants-1996_01
Patent number
US05486610

Reaction notes

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