Acetonitrile → HCID 18973085, compound

HRID 2394359Notes

Reaction equation

HRID 2394359 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH:5]2[C:12](=[O:19])[C:13]1[S:17][CH:16]=[C:15]([Cl:18])[CH:14]=1.[C:20](=[O:26])=[N:21]S(Cl)(=O)=O.C(#N)C.ClS(NC=O)(=O)=O>CS(C)=O.O>[Cl:1][C:2]1[N:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:20]([NH2:21])=[O:26])[C:6](=[O:11])[CH:5]2[C:12](=[O:19])[C:13]1[S:17][CH:16]=[C:15]([Cl:18])[CH:14]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 70918Chlorosulfonyl isocyanateHCID 15228322HCID 15228322, compoundHCID 18973027HCID 18973027, compound2×

Product 1

HCID 18973085HCID 18973085, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The title compound was prepared from 5-chloro-3-(4-chloro-2-thenoyl)-4-azaoxindole (Example 27) according to the procedure of Example 2C, using 5-chloro-3-(4-chloro-2-thenoyl)-4-azaoxindole (0.75 g, 2.39 mmol), N-chlorosulfonyl isocyanate (0.31 mL, 3.56 mmol), and acetonitrile (12 mL). Hydrolysis of the N-chlorosulfonyl carboxamide was achieved by stirring in DMSO (8 mL) for 4 hours at room temperature in a flask open to the air. The product was obtained by dilution of the mixture with water followed by filtration and recrystallized from acetic acid. Yield: 352 mg (41%).

Workup

  1. filtrationfollowed by filtration
  2. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-2f33355e6c9d4df2899fd48e53492796
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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