Potassium Carbonate → 5-Amino-1-(2-ethylsulfanyl-ethyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one

HRID 2235374Notes

Reaction equation

HRID 2235374 reaction equation
[CH3:1][C:2]1([CH3:19])[C:10]2[C:5](=[CH:6][C:7]([N+:15]([O-:17])=[O:16])=[C:8]([NH:11]C(=O)C)[CH:9]=2)[NH:4][C:3]1=[O:18].Cl[CH2:21][CH2:22][S:23][CH2:24][CH3:25].C([O-])([O-])=O.[K+].[K+]>>[NH2:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16])[N:4]([CH2:21][CH2:22][S:23][CH2:24][CH3:25])[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 127332-Chloroethyl ethyl sulfideHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 593010075-Amino-1-(2-ethylsulfanyl-ethyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-oneYield 55.3%

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (1 g) is alkylated using 1-chloro-2-ethylsulfanyl-ethane (0.5 ml; 3.83 mmol) and K2CO3 (0.54 g; 3.83 mmol) at 40° C. for 4 d. After aqueous work-up and purification by RP chromatography the pure material (0.77 g) is de-acetylated in MeOH (35 ml) using DBU (0.3 ml) at reflux. After aqueous work-up 5-amino-1-(2-ethylsulfanyl-ethyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (0.65 g) is obtained and used without further purification.

Workup

  1. customat 40° C.
  2. customfor 4 d
  3. customAfter aqueous work-up and purification by RP chromatography the pure material (0.77 g)
  4. temperatureat reflux

Sources & evidence

ORD record
ord-446df5ba0a354621ab21e11178288f2c
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

Loading…