Sodium hydride → 1-(4,5-Dihydro-1,3-thiazol-2-yl)-1,3-dihydro-2H-indol-2-one

HRID 972747Notes

Reaction equation

HRID 972747 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[H-].[Na+].Cl[CH2:14][CH2:15][N:16]=[C:17]=[S:18]>C(COC)OC>[S:18]1[CH2:14][CH2:15][N:16]=[C:17]1[N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1386612-Chloroethyl IsothiocyanateHCID 321710Oxindole

Product 1

HCID 214055041-(4,5-Dihydro-1,3-thiazol-2-yl)-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of 4.0 g (0.03 mole) of oxindole in 125 ml dry glyme there is added 1.4 g (0.03 mole) of sodium hydride (50% oil dispersion) and the mixture is stirred at room temperature for 3 hours. 3.6 g (0.3 Mole) of 2-chloroethyl isothiocyanate in 5 ml of dry glyme is then added and the mixture is refluxed overnight. After evaporation of the solvent in vacuo, the residue is chromatographed on an Alumina Act. IV column. Elution with ethyl ether yields the product which is crystallized from ethyl ether to yield 0.6 g, m.p. 97°-99°.

Workup

  1. temperaturethe mixture is refluxed overnight
  2. customAfter evaporation of the solvent in vacuo
  3. customthe residue is chromatographed on an Alumina Act
  4. washElution with ethyl ether
  5. customyields the product which
  6. customis crystallized from ethyl ether
  7. customto yield 0.6 g, m.p. 97°-99°

Sources & evidence

ORD record
ord-bf867c3ab3eb46d9a318fd1e5fd39e66
Source dataset
uspto-grants-1977_10
Patent number
US04053613

Reaction notes

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