Acetonitrile → HCID 18973071, compound

HRID 2394366Notes

Reaction equation

HRID 2394366 reaction equation
[C:1]1([CH2:7][C:8]([CH:10]2[C:18]3[C:13](=[CH:14][N:15]=[CH:16][CH:17]=3)[NH:12][C:11]2=[O:19])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20](=[O:26])=[N:21]S(Cl)(=O)=O.C(#N)C.ClS(NC=O)(=O)=O>CS(C)=O>[C:1]1([CH2:7][C:8]([CH:10]2[C:18]3[C:13](=[CH:14][N:15]=[CH:16][CH:17]=3)[N:12]([C:20]([NH2:21])=[O:26])[C:11]2=[O:19])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 70918Chlorosulfonyl isocyanateHCID 15228322HCID 15228322, compoundHCID 18973048HCID 18973048, compound2×

Product 1

HCID 18973071HCID 18973071, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared from 3-phenylacetyl-6-azaoxindole according to the procedure of Example 2C, using 3-phenylacetyl-6-azaoxindole (1.0 g, 3.9 mmol), N-chlorosulfonyl isocyanate (0.41 mL, 4.7 mmol) and acetonitrile (40 mL). Reaction time: 4 hours. The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in DMSO (6 mL) for 1 hour in a flask open to the air. After dilution with water, the product was collected by filtration, dried, and recrystallized from acetic acid. Yield: 172 mg (15%). M.p. 131°-133° C. (dec.).

Workup

  1. customReaction time
  2. custom4 hours
  3. filtrationAfter dilution with water, the product was collected by filtration
  4. customdried
  5. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-d1323a4048644d74a06192be1371b901
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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