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

HRID 978684Notes

Reaction equation

HRID 978684 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 to said mixture with good stirring for ten minutes. The aqueous solution was extracted with ethyl acetate (600 ml), 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. stirringwith good stirring for ten minutes
  2. extractionThe aqueous solution was extracted with ethyl acetate (600 ml)
  3. washwashed successively with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto give a gray solid which
  7. customwas recrystallized from acetonitrile Yield=3.0 g

Sources & evidence

ORD record
ord-0fa7d40d21194116a1601424b07ca8fb
Source dataset
uspto-grants-1987_05
Patent number
US04665194

Reaction notes

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