Chlorosulfonyl isocyanate → HCID 18973116, compound

HRID 2394364Notes

Reaction equation

HRID 2394364 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6](=[O:12])[CH:5]2[C:13](=[O:19])[C:14]1[S:18][CH:17]=[CH:16][CH:15]=1.[C:20](=[O:26])=[N:21]S(Cl)(=O)=O.ClS(NC=O)(=O)=O>CS(C)=O>[Cl:1][C:2]1[N:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[N:7]([C:20]([NH2:21])=[O:26])[C:6](=[O:12])[CH:5]2[C:13](=[O:19])[C:14]1[S:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 70918Chlorosulfonyl isocyanateHCID 15228322HCID 15228322, compoundHCID 18973115HCID 18973115, compound2×

Product 1

HCID 18973116HCID 18973116, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared from 5,6-dichloro-3-(2-thenoyl)-4-azaoxindole (Example 6B) according to the procedure of Example 2C, using 5,6-dichloro-3-(2-thenoyl)-4-azaoxindole (194 mg, 0.62 mmol), N-chlorosulfonyl isocyanate (81 L, 0.93 mmol) acetonitrile (10 mL), and a temperature of 50° C. The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in DMSO in a flask open to the air. After dilution with water, the solid was collected by filtration and recrystallized from acetic acid. Yield: 129 mg (58%).

Workup

  1. customa temperature of 50° C
  2. filtrationAfter dilution with water, the solid was collected by filtration
  3. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-3f66f73ef73e4cddb07a73d1cbed2168
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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