Chlorosulfonyl isocyanate → HCID 20405594, compound

HRID 2164417Notes

Reaction equation

HRID 2164417 reaction equation
[C:1](=[O:7])=[N:2][S:3]([Cl:6])(=[O:5])=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)(=[O:18])=[O:17])=[CH:11][C:10]=1[N+:29]([O-:31])=[O:30]>C1(C)C=CC=CC=1>[Cl:6][S:3]([NH:2][C:1](=[O:7])[NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)(=[O:17])=[O:18])=[CH:11][C:10]=1[N+:29]([O-:31])=[O:30])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 13145814HCID 13145814, compound

Product 1

HCID 20405594HCID 20405594, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

30 ml of N-chlorosulfonyl isocyanate are added dropwise, at +10° C., to 108 g of 2-amino-5-(3-trifluoromethylphenylsulfonyloxy)nitrobenzene in 800 ml of toluene. The mixture is stirred for a further two hours while cooling, and 500 ml of petroleum ether are added. The 2-(3-chlorosulfonylureido)-5-(3-trifluoromethylphenylsulfonyloxy)nitrobenzene produced is filtered off with suction, washed with petroleum ether and dried over potassium hydroxide, melting point 137° C., decomposition. 150 g of this sulfochloride are introduced, with stirring and cooling in ice, into 2 liters of 1N HCl. The mixture is stirred for 2 hours while cooling and for 5 hours at room temperature, and next day the precipitate is filtered off with suction, washed with water to neutrality and dried, melting point 152° C.

Workup

  1. temperaturewhile cooling

Sources & evidence

ORD record
ord-87f567a010b64259ae0573954fad5d5d
Source dataset
uspto-grants-1985_03
Patent number
US04504490

Reaction notes

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