Chlorosulfonyl isocyanate → HCID 20405591, compound

HRID 2164410Notes

Reaction equation

HRID 2164410 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]([S:15]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:17])=[O:16])=[CH:11][C:10]=1[N+:25]([O-:27])=[O:26]>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]([S:15]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:17])=[O:16])=[CH:11][C:10]=1[N+:25]([O-:27])=[O:26])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 15585381HCID 15585381, compound

Product 1

HCID 20405591HCID 20405591, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

30 ml of N-chlorosulfonyl isocyanate dissolved in 70 ml of toluene are rapidly added dropwise, at +10° C., to 88.2 g of 2-amino-5-phenoxysulfonylnitrobenzene in 750 ml of toluene. The mixture is stirred for a further hour while cooling, and the precipitate is filtered off with suction, washed with diisopropyl ether and dried in a desiccator over potassium hydroxide. 88 g of the 2-(3-chlorosulfonylureido)-5-phenoxysulfonylnitrobenzene produced are introduced, with stirring and cooling, into 800 ml of 1N HCl. After 30 minutes, the clear solution is briefly warmed to 80° C. (precipitation) and then left to stand. After cooling down, the solid is filtered off with suction and washed with water to neutrality, melting point 190° C.

Workup

  1. temperaturewhile cooling
  2. filtrationthe precipitate is filtered off with suction
  3. washwashed with diisopropyl ether
  4. dry with materialdried in a desiccator over potassium hydroxide

Sources & evidence

ORD record
ord-857e7bb5de36482193c0e63f9f7daebb
Source dataset
uspto-grants-1985_03
Patent number
US04504490

Reaction notes

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