Chlorosulfonyl isocyanate → 2-Oxindole-1-carboxamide

HRID 978680Notes

Reaction equation

HRID 978680 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 77.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Chlorosulfonyl isocyanate (1.20 g, 8.4 mmoles) was added to a mixture of 2-oxindole (0.94 g, 7.1 mmole) in ether (30 ml) and the reaction stirred at room temperature for 20 hours. The ether was removed under vacuum and the residue treated with water (10 ml) and 1N HCl (10 ml). Ethyl acetate (125 ml) was added and the mixture 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; m.p. 178°-180° C.

Workup

  1. customThe ether was removed under vacuum
  2. additionthe residue treated with water (10 ml) and 1N HCl (10 ml)
  3. additionEthyl acetate (125 ml) was added
  4. stirringthe mixture 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

Sources & evidence

ORD record
ord-46f779bb15834addbbf24200e9d8613a
Source dataset
uspto-grants-1987_05
Patent number
US04665194

Reaction notes

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