Chlorosulfonyl isocyanate → HCID 18973107, compound

HRID 2394358Notes

Reaction equation

HRID 2394358 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]([C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)=[O:13].[C:19](=[O:25])=[N:20]S(Cl)(=O)=O.ClS(NC=O)(=O)=O>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:19]([NH2:20])=[O:25])[C:6](=[O:11])[CH:5]2[C:12]([C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)=[O:13]

Participants

5

Reactant 3

HCID 70918Chlorosulfonyl isocyanateHCID 15228322HCID 15228322, compoundHCID 18973022HCID 18973022, compound2×

Product 1

HCID 18973107HCID 18973107, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared from 5-chloro-3-(2-furoyl)-4-azaoxindole (Example 23) according to the procedure of Example 2C, using 5-chloro-3-(2-furoyl)-4-azaoxindole (200 mg, 0.76 mmol), N-chlorosulfonyl isocyanate (0.10 mL, 1.1 mmol) and acetonitrile (8 mL). Hydrolysis of the N-chlorosulfonyl carboxamide was achieved by quenching the above reaction with water and allowing the mixture to stir at room temperature overnight. The product was collected by filtration and recrystallized from DMSO. Yield: 75 mg (32%).

Workup

  1. customby quenching
  2. customthe above reaction with water
  3. filtrationThe product was collected by filtration
  4. customrecrystallized from DMSO

Sources & evidence

ORD record
ord-14c579e251cf452ab252bb9e3b2f2a2f
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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