Acetonitrile → HCID 18973045, compound

HRID 2394361Notes

Reaction equation

HRID 2394361 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12](=[O:18])[C:13]3[S:17][CH:16]=[CH:15][CH:14]=3)[C:7](=[O:11])[NH:8]2)=[N:4][CH:3]=1.[C:19](=[O:25])=[N:20]S(Cl)(=O)=O.C(#N)C.ClS(NC=O)(=O)=O>CS(C)=O.O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12](=[O:18])[C:13]3[S:17][CH:16]=[CH:15][CH:14]=3)[C:7](=[O:11])[N:8]2[C:19]([NH2:20])=[O:25])=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 70918Chlorosulfonyl isocyanateHCID 15228322HCID 15228322, compoundHCID 18973072HCID 18973072, compound2×

Product 1

HCID 18973045HCID 18973045, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The title compound was prepared from 6-fluoro-3-(2-thenoyl)-4-azaoxindole (Example 5) according to the procedure of Example 2C, using 6-fluoro-3-(2-thenoyl)-4-azaoxindole (419 mg, 1.60 mmol), N-chlorosulfonyl isocyanate (0.2 mL, 2.3 mmol), and acetonitrile (8 mL). Reaction time: 3 days. The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in DMSO in a flask open to the air, diluting with water, and collecting the product by filtration. The product was recrystallized from acetic acid. Yield: 210 mg (43%).

Workup

  1. customReaction time
  2. custom3 days
  3. customcollecting the product
  4. filtrationby filtration
  5. customThe product was recrystallized from acetic acid

Sources & evidence

ORD record
ord-28c3946abe284871ae432def833c18a7
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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