Hydrochloric Acid → HCID 44603793, compound

HRID 2425002Notes

Reaction equation

HRID 2425002 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]([S:13]([N:16]2[C:24]3[C:19](=[CH:20][C:21]([O:25][CH3:26])=[CH:22][CH:23]=3)[C:18]([CH3:27])=[CH:17]2)(=[O:15])=[O:14])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])(=O)C.Cl>C(O)C>[NH2:4][C:5]1[CH:6]=[C:7]([S:13]([N:16]2[C:24]3[C:19](=[CH:20][C:21]([O:25][CH3:26])=[CH:22][CH:23]=3)[C:18]([CH3:27])=[CH:17]2)(=[O:14])=[O:15])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67245854HCID 67245854, compound

Product 1

HCID 44603793HCID 44603793, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(3′-Acetamido-4′-methoxybenzenesulfonyl)-5-methoxy-3-methyl-1H-indole (10 grams, 25.7 mmol) (obtained from preparation 1) was taken into a 250 mL of three necked round bottom flask containing ethanol (100 mL) and stirred the mass to obtain a clear solution. Aqueous hydrochloric acid (10 mL, 33%) was added to this clear solution and heated the mass at reflux temperature for a period of two hours. The progress of the reaction was monitored by thin layer chromatography. After completion of the reaction, the reaction mass was concentrated under vacuum and the residual mass was quenched into chilled water (100 mL). The pH was adjusted to 9.0 to 10.0 with dilute sodium hydroxide solution. The product was extracted with dichloro methane (2×100 mL). Organic phase was washed with brine solution, dried over anhydrous sodium sulphate and concentrated the mass under reduced pressure to obtain crude compound. The obtained technical product was purified by column chromatography using silica gel (100-200 mesh), the eluent system being ethyl acetate and n-hexane (2:8) to obtain 1.0 gram of the title product.

Workup

  1. customto obtain a clear solution
  2. temperatureheated the mass
  3. temperatureat reflux temperature for a period of two hours
  4. customAfter completion of the reaction
  5. concentrationthe reaction mass was concentrated under vacuum
  6. customthe residual mass was quenched
  7. temperatureinto chilled water (100 mL)
  8. extractionThe product was extracted with dichloro methane (2×100 mL)
  9. washOrganic phase was washed with brine solution
  10. dry with materialdried over anhydrous sodium sulphate
  11. concentrationconcentrated the mass under reduced pressure
  12. customto obtain crude compound
  13. customThe obtained technical product was purified by column chromatography

Sources & evidence

ORD record
ord-41d709908fe94ee4b77ba386574b1bc9
Source dataset
uspto-grants-2011_06
Patent number
US07964627B2

Reaction notes

Loading…