Chlorosulfonyl isocyanate → HCID 18973105, compound

HRID 2394368Notes

Reaction equation

HRID 2394368 reaction equation
C1(C(C2C3C(=CC=CN=3)[NH:10][C:9]2=[O:17])=O)SC=CC=1.[C:18]1([C:23]([CH:25]2[C:33]3[C:28](=[CH:29][CH:30]=[N:31][CH:32]=3)[NH:27][C:26]2=[O:34])=[O:24])[S:22][CH:21]=[CH:20][CH:19]=1.C(=O)=NS(Cl)(=O)=O.ClS(NC=O)(=O)=O>CS(C)=O.CO.CCOCC.C(#N)C>[C:18]1([C:23]([CH:25]2[C:33]3[C:28](=[CH:29][CH:30]=[N:31][CH:32]=3)[N:27]([C:9]([NH2:10])=[O:17])[C:26]2=[O:34])=[O:24])[S:22][CH:21]=[CH:20][CH:19]=1

Participants

9

Reactant 4

HCID 70918Chlorosulfonyl isocyanateHCID 15228322HCID 15228322, compoundHCID 18973016HCID 18973016, compoundHCID 18973078HCID 18973078, compound

Product 1

HCID 18973105HCID 18973105, compound

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared from 3-(2-thenoyl)-4-azaoxindole (Example 4C) according to the procedure of Example 2C, using 3-(2-thenoyl)-5-azaoxindole (500 mg, 2.0 mmol), N-chlorosulfonyl isocyanate (0.26, 3.0 mmol), and acetonitrile (15 mL). Reaction time: 2.25 hours. The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in DMSO (1.5 mL) for 1.5 hours in a flask open to the air. Ether was added to give a two phase mixture followed by methanol, which gave a homogenous solution. On standing for a brief period, a green precipitate formed which was removed by filtration. The filtrate was allowed to stand overnight, during which time the product crystallized from the solution. This was collected by filtration. Yield: 39 mg (7%). M.p. 250°.

Workup

  1. customReaction time
  2. custom2.25 hours
  3. customto give a two phase mixture
  4. customgave a homogenous solution
  5. waitOn standing for a brief period
  6. customa green precipitate formed which
  7. customwas removed by filtration
  8. customthe product crystallized from the solution
  9. filtrationThis was collected by filtration

Sources & evidence

ORD record
ord-c1e1a56562d049da98450e52a9619ad1
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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