Acetonitrile → HCID 18973075, compound

HRID 2394367Notes

Reaction equation

HRID 2394367 reaction equation
[CH:1]([O:4][C:5]1[N:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH:8]2[C:15](=[O:21])[C:16]1[S:20][CH:19]=[CH:18][CH:17]=1)([CH3:3])[CH3:2].[C:22](=[O:28])=[N:23]S(Cl)(=O)=O.C(#N)C.ClS(NC=O)(=O)=O>C(Cl)(Cl)Cl>[CH:1]([O:4][C:5]1[N:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:22]([NH2:23])=[O:28])[C:9](=[O:14])[CH:8]2[C:15](=[O:21])[C:16]1[S:20][CH:19]=[CH:18][CH:17]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 70918Chlorosulfonyl isocyanateHCID 15228322HCID 15228322, compoundHCID 18973020HCID 18973020, compound2×

Product 1

HCID 18973075HCID 18973075, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared from 5-isopropoxy-3-(2-thenoyl)-4-azaoxindole (Example 9C) according to the procedure of Example 2C, using 5-isopropoxy-3-(2-thenoyl)-4-azaoxindole (70 mg, 0.23 mmol), N-chlorosulfonyl isocyanate (25 L, 0.29 mmol) and acetonitrile (1.5 mL). Reaction time: 4 hours. The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in chloroform for 3 days. After removal of the solvent in vacuo, the product was purified by flash chromatography on silica gel using 2:1 ethyl acetate/hexane as eluant and trituration with ether. Yield: 30 mg (37%). M.p. 194°-196° C.

Workup

  1. customReaction time
  2. custom4 hours
  3. customAfter removal of the solvent in vacuo
  4. customthe product was purified by flash chromatography on silica gel using 2:1 ethyl acetate/hexane as eluant

Sources & evidence

ORD record
ord-6b367e8b82584560961988b14362c1de
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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