Acetonitrile → HCID 18973024, compound

HRID 2394353Notes

Reaction equation

HRID 2394353 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)=[O:13])[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.C(O)(=O)C.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)=[O:13])[C:7](=[O:11])[N:8]2[C:19]([NH2:20])=[O:25])=[N:4][CH:3]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 70918Chlorosulfonyl isocyanateHCID 15228322HCID 15228322, compoundHCID 18973061HCID 18973061, compound2×

Product 1

HCID 18973024HCID 18973024, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The title compound was prepared from 6-chloro-3-(2-furoyl)-4-azaoxindole (Example 12) according to the procedure of Example 2C, using 400 mg (1.5 mmol) 6-chloro-3-(2-furoyl)-4-azaoxindole, 0.19 ml (2.25 mmol) N-chlorosulfonyl isocyanate and 15 ml acetonitrile. The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in DMSO (5 ml), for 2 hours in a flask open to the air. The product was isolated by dilution with water filtration, and recrystallization from acetic acid. Yield: 160 mg (35%).

Sources & evidence

ORD record
ord-9692c5c7950f472b92c4b1f35878f491
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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