Tetrahydrofuran → HCID 14183544, compound

HRID 1722261Notes

Reaction equation

HRID 1722261 reaction equation
[CH2:1]([O:3][C:4](Cl)=[O:5])[CH3:2].[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[C:11]2=[O:18].O1CCCC1>C(N(CC)CC)C>[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:12](=[O:17])[C:11]2=[O:18]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 872035-chloro-1H-indole-2,3-dione

Product 1

HCID 14183544HCID 14183544, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Ethoxycarbonyl chloride (10.5 ml) is added dropwise to a mixture of 5-chloroisatin (18.16 g), tetrahydrofuran (180 ml) and triethylamine (15.3 ml) with stirring, and the mixture is stirred at room temperature for 5 minutes. The mixture is concentrated under reduced pressure to remove solvent, and water is added to the residue. Crystalline precipitates are collected by filtration, washed with isopropanol and isopropyl ether and then dried, whereby 5-chloro-1-ethoxycarbonylisatin (23.3 g) is obtained.

Workup

  1. stirringthe mixture is stirred at room temperature for 5 minutes
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customto remove solvent, and water
  4. additionis added to the residue
  5. customCrystalline precipitates
  6. filtrationare collected by filtration
  7. washwashed with isopropanol and isopropyl ether
  8. customdried

Sources & evidence

ORD record
ord-688bda8ea62742089b63909c11d7d940
Source dataset
uspto-grants-1989_08
Patent number
US04855298

Reaction notes

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