4-Chloroaniline → 5-Chloro-3-(ethylsulfanyl)-3-(2-hydroxyethyl)-1,3-dihydro-2H-indol-2-one

HRID 25969

Reaction equation

HRID 25969 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.ClOC(C)(C)C.[CH2:15]([S:17][CH:18]1[CH2:23][CH2:22][O:21][C:19]1=[O:20])[CH3:16].C(N(CC)CC)C>C(Cl)Cl.O>[Cl:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][CH:3]=1)[NH:6][C:19](=[O:20])[C:18]2([CH2:23][CH2:22][OH:21])[S:17][CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 8471TriethylamineHCID 521297Tert-Butyl hypochloriteHCID 108772592-Ethylmercaptobutyrolactone

Product 1

HCID 128664185-Chloro-3-(ethylsulfanyl)-3-(2-hydroxyethyl)-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent4×

Procedure

To the stirred solution of 5.6 g p-chloroaniline in 150 ml of methylene chloride is added dropwise 4.7 ml of t-butyl hypochlorite in 20 ml of methylene chloride at -65°. After ten minutes, the solution of 5.75 g of 2-ethylmercaptobutyrolactone in 20 ml of methylene chloride is added dropwise and the temperature held at -65° for two hours. Then the solution of 6.1 ml of triethylamine in 20 ml of methylene chloride is added dropwise and the mixture is allowed to warm up to room temperature. 50 ml of water are added with stirring and the precipitate filtered off, to yield the 5-chloro-3-(2-hydroxyethyl)-3-ethylmercapto-2-oxindole melting at 132°-135°.

Workup

  1. waitAfter ten minutes
  2. filtrationthe precipitate filtered off

Sources & evidence

ORD record
ord-f96e9ff5ba8147c991cb80b144fa53c2
Source dataset
uspto-grants-1979_04
Patent number
US04147786

Linked notes

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