Potassium Carbonate → HCID 86740889, compound
Reaction equation
[C:1]([S:4][CH2:5][CH2:6][C:7](Cl)=[O:8])(=[O:3])[CH3:2].[CH2:10]([O:12][C:13]([CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][C:19]([O:26][CH3:27])=[C:20]([O:24][CH3:25])[CH:21]=2)[NH:16]1)=[O:14])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH2:10]([O:12][C:13]([CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][C:19]([O:26][CH3:27])=[C:20]([O:24][CH3:25])[CH:21]=2)[N:16]1[C:7](=[O:8])[CH2:6][CH2:5][S:4][C:1](=[O:3])[CH3:2])=[O:14])[CH3:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The solution of 3.6 g of 3-acetylthiopropanoyl chloride in 10 ml of methylene chloride is added dropwise while stirring under nitrogen to the suspension of 5.4 g of 5,6-dimethoxyindoline-2-carboxylic acid ethyl ester and 5.96 g of powdered potassium carbonate in 40 ml of methylene chloride. The mixture is stirred for 2 hours at room temperature, filtered and the filtrate washed successively with saturated aqueous sodium bicarbonate, water, 0.5N hydrochloric acid and water. The organic solution is dried, evaporated, the residue crystallized from petroleum ether and further purified by slurrying in diethyl ether for 2 hours, to yield the 1-(3-acetylthiopropanoyl)-5,6-dimethoxyindoline-2-carboxylic acid ethyl ester melting at 104°-106°.
Workup
- filtrationfiltered
- washthe filtrate washed successively with saturated aqueous sodium bicarbonate, water, 0.5N hydrochloric acid and water
- customThe organic solution is dried
- customevaporated
- customthe residue crystallized from petroleum ether
- customfurther purified
- waitby slurrying in diethyl ether for 2 hours
Sources & evidence
- ORD record
- ord-6f71eddc2fc34937860e74b8de3d24da
- Source dataset
- uspto-grants-1986_07
- Patent number
- US04599357
Reaction notes
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