Acetonitrile → HCID 18973015, compound

HRID 2394363Notes

Reaction equation

HRID 2394363 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][N:10]=1)[NH:7][C:6](=[O:11])[CH:5]2[C:12](=[O:18])[C:13]1[S:17][CH:16]=[CH:15][CH:14]=1.[C:19](=[O:25])=[N:20]S(Cl)(=O)=O.C(#N)C.ClS(NC=O)(=O)=O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][N:10]=1)[N:7]([C:19]([NH2:20])=[O:25])[C:6](=[O:11])[CH:5]2[C:12](=[O:18])[C:13]1[S:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 70918Chlorosulfonyl isocyanateHCID 15228322HCID 15228322, compoundHCID 18973026HCID 18973026, compound2×

Product 1

HCID 18973015HCID 18973015, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared from 5-chloro-3-(2-thenoyl)-6-azaoxindole (Example 3C) according to the procedure of Example 2C, using 5-chloro-3-(2-thenoyl)-6-azaoxindole (140 mg, 0.5 mmol), N-chlorosulfonyl isocyanate (65 L, 0.75 mmol), and acetonitrile (5 mL). The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in DMSO for 2 hours in a flask open to the air. The product was precipitated by addition of water and was collected by filtration. The solid was recrystallized from methanol. Yield: 27 mg (17%).

Workup

  1. customThe product was precipitated by addition of water
  2. filtrationwas collected by filtration
  3. customThe solid was recrystallized from methanol

Sources & evidence

ORD record
ord-71cc279e2c6c40b498aad28701ffa850
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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