Water → 6-Methylthio-2-oxindole-1-carboxamide

HRID 637349Notes

Reaction equation

HRID 637349 reaction equation
Cl[S:2](N=C=O)(=O)=O.[CH3:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][C:14](=S)[NH:15]2)=[CH:11][CH:10]=1.[OH2:19].[C:20](#[N:22])C>>[CH3:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][C:14](=[O:19])[N:15]2[C:20]([NH2:22])=[S:2])=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 70918Chlorosulfonyl isocyanateHCID 212820706-Methylthiooxindole

Product 1

HCID 867405216-Methylthio-2-oxindole-1-carboxamide

Procedure

Chlorosulfonyl isocyanate (5.66 g, 0.04 mole) was added to a slurry of 6-methylthio-2-oxindole (6.0 g, 0.033 mole) in acetonitrile (60 ml) at 5° to 10° C. The reaction mixture was stirred for one hour. Water (100 ml) was then added and stirring was continued for ten minutes. The aqueous solution was extracted with ethyl acetate (600 ml), which was then washed successively with water and brine, dried (MgSO4) and evaporated under reduced pressure to give a gray solid which was recrystallized from acetonitrile. Yield=3.0 g. An additional 0.71 g of product was obtained from the mother liquor. Total yield=3.71 g (50.6%); m.p. 176°-179° C.

Workup

  1. stirringstirring
  2. waitwas continued for ten minutes
  3. extractionThe aqueous solution was extracted with ethyl acetate (600 ml), which
  4. washwas then washed successively with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customto give a gray solid which
  8. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-87566699f9cb43839b1afdb6ef50518d
Source dataset
uspto-grants-1985_12
Patent number
US04556672

Reaction notes

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