Dichloromethane → HCID 23313826, compound

HRID 745613Notes

Reaction equation

HRID 745613 reaction equation
C([O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]3[O:17][CH2:16][O:15][C:11]=3[CH:12]=2)[NH:7]1)=[O:5])C.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl.C([S:30][CH2:31][CH:32]([CH3:36])[C:33](Cl)=[O:34])(=O)C>C(OCC)C>[SH:30][CH2:31][CH:32]([CH3:36])[C:33]([N:7]1[C:8]2[C:13](=[CH:12][C:11]3[O:15][CH2:16][O:17][C:10]=3[CH:9]=2)[CH2:14][CH:6]1[C:4]([O-:3])=[O:5])=[O:34].[CH:8]1([NH2+:7][CH:6]2[CH2:4][CH2:33][CH2:32][CH2:31][CH2:14]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 53672576HCID 53672576, compound

Product 1

HCID 23313826HCID 23313826, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the mixture of 0.65 g of 5,6-methylenedioxyindoline-2-carboxylic acid ethyl ester, 0.76 g of powdered potassium carbonate and 8 ml of methylene chloride is added 0.50 g of 3-acetylthio-2-methylpropanoyl chloride while stirring at room temperature. It is refluxed for 2 hours, poured into 16 ml of diethyl ether and washed with 8 ml of water, 8 ml of N hydrochloride acid and 8 ml of saturated aqueous sodium bicarbonate. The organic phase is separated, dried and evaporated. The residue is taken up in 5 ml of methanol and 4.0 ml of 2.03N aqueous potassium hydroxide are each deoxygenated by bubbling nitrogen through the solutions for 10 minutes. The latter solution is added to the former and the mixture stirred at room temperature under nitrogen. After 2 hours, 15 ml of 2N hydrochloric acid are added and the mixture is extracted thrice with 25 ml of diethyl ether. The extract is dried, evaporated, the residue taken up in 10 ml of diethyl ether and the solution combined with 0.44 g of dicyclohexylamine, producing a white precipitate. It is collected, washed thrice with 3 ml of diethyl ether and dried to give the dicyclohexylammonium 1-(3-mercapto-2-methylpropanoyl)-5,6-methylenedioxyindoline-2-carboxylate melting at 194°-196°.

Workup

  1. temperatureIt is refluxed for 2 hours
  2. washwashed with 8 ml of water, 8 ml of N hydrochloride acid and 8 ml of saturated aqueous sodium bicarbonate
  3. customThe organic phase is separated
  4. customdried
  5. customevaporated
  6. customeach deoxygenated
  7. customby bubbling nitrogen through the solutions for 10 minutes
  8. additionThe latter solution is added to the former and the mixture
  9. stirringstirred at room temperature under nitrogen
  10. addition15 ml of 2N hydrochloric acid are added
  11. extractionthe mixture is extracted thrice with 25 ml of diethyl ether
  12. customThe extract is dried
  13. customevaporated
  14. customproducing a white precipitate
  15. customIt is collected
  16. washwashed thrice with 3 ml of diethyl ether
  17. customdried

Sources & evidence

ORD record
ord-6f3510eb857644138b43ebba49f2c8a8
Source dataset
uspto-grants-1986_07
Patent number
US04599357

Reaction notes

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