Chlorosulfonyl isocyanate → 2-Oxindole-1-carboxamide

HRID 637345Notes

Reaction equation

HRID 637345 reaction equation
ClS([N:5]=[C:6]=[O:7])(=O)=O.[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C:9]1=[O:17]>CCOCC>[N:8]1([C:6]([NH2:5])=[O:7])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C:9]1=[O:17]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 321710Oxindole

Product 1

HCID 115172742-Oxindole-1-carboxamideYield 14.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Chlorosulfonyl isocyanate (1.20 g, 8.4 mmole) was added to a mixture of 2-oxindole (0.94 g, 7.1 mmole) in ether (30 ml) and the reaction was stirred at room temperature for 20 hours. The ether was removed under vacuum and the residue was treated with water (10 ml) and 1N HCl (10 ml). Ethyl acetate (125 ml) was added and the mixture was stirred for one hour. The ethyl acetate phase was separated, washed with 1N HCl (1×50 ml), brine (2×100 ml) and dried (MgSO4). Concentration afforded 0.97 g (77%) of crude product. Recrystallization from ethanol gave 0.18 g of the title product, m.p. 177°-179° C.

Workup

  1. customThe ether was removed under vacuum
  2. additionthe residue was treated with water (10 ml) and 1N HCl (10 ml)
  3. additionEthyl acetate (125 ml) was added
  4. stirringthe mixture was stirred for one hour
  5. customThe ethyl acetate phase was separated
  6. washwashed with 1N HCl (1×50 ml), brine (2×100 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationConcentration
  9. customafforded 0.97 g (77%) of crude product
  10. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-03ef0c9ba91a4969a63628d7bac35ad6
Source dataset
uspto-grants-1985_12
Patent number
US04556672

Reaction notes

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