Hydrochloric Acid → HCID 20441671, compound

HRID 1633138Notes

Reaction equation

HRID 1633138 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH3:24])=[C:16]2[C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[CH:8][CH:7]=1)=[O:5])C.C([O-])(O)=O.[Na+].CCOCC.[ClH:41]>>[ClH:41].[C:4]([C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH3:24])=[C:16]2[C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[CH:8][CH:7]=1)([OH:5])=[O:3]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 13362111HCID 13362111, compound

Product 1

HCID 20441671HCID 20441671, compound

Procedure

A mixture of 6.39 g of 1-[2-(4-ethoxycarbonylphenylthio)ethyl]-2-(3-pyridyl)-3-methylindole in 260 ml of 2 N HCl is heated at reflux temperature for 6 hours. After cooling the pH is adjusted to 6-7 with saturated aqueopus NaHCO3 (ca 500 ml). About 200 ml of ether is added and the mixture is stirred for 0.5 hour. A solid is collected, first washed with water, then ether, and then dissolved in 100 ml hot absolute ethanol. The solution is filtered, and while still hot treated with 1.68 ml of 6.5 N ethanolic HCl. The solution is cooled and diluted with ca 100 ml ether. The resulting product is collected to yield 1-[2-(4-carboxyphenylthio)ethyl]-2-(3-pyridyl)-3-methylindole hydrochloride, m.p. 222°-224°.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 6 hours
  3. temperatureAfter cooling the pH
  4. customA solid is collected
  5. washfirst washed with water
  6. dissolutionether, and then dissolved in 100 ml hot absolute ethanol
  7. filtrationThe solution is filtered
  8. additionwhile still hot treated with 1.68 ml of 6.5 N ethanolic HCl
  9. temperatureThe solution is cooled
  10. additiondiluted with ca 100 ml ether
  11. customThe resulting product is collected

Sources & evidence

ORD record
ord-4b8cf5925a244bdf80e425d547eb6ad0
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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