Ethanol → HCID 14032988, compound

HRID 2414108Notes

Reaction equation

HRID 2414108 reaction equation
BrC(=O)[CH:3]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2)[CH2:4][CH3:5].[NH2:18][C:19]([NH2:21])=[S:20].[CH2:22](O)C>>[NH2:18][C:19]1[S:20][C:4]([CH2:5][CH3:22])=[C:3]([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]3)[N:21]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 2723790ThioureaHCID 131715438HCID 131715438, compound

Product 1

HCID 14032988HCID 14032988, compound

Procedure

A mixture of 6-(α-bromobutanoyl)-3,4-dihydrocarbostyril (7 g), thiourea (1.9 g) and absolute ethanol (250 ml) is stirred at reflux for 4 hours. The reaction mixture is cooled in an ice bath and the solid filtered, washed with ether, dried and suspended in aqueous sodium bicarbonate for 30 minutes. The neutralized solid is filtered, washed with water and isopropanol, and dried. The dried solid is suspended in boiling THF to which methane sulfonic acid is added. The resulting THF solution is concentrated and cooled in an ice bath resulting in the formation of a precipitate which is filtered, washed with ether, dried in vacuo and twice recrystallized from acetonitrile and isopropanol affording the desired product as the methane sulfonic salt, M.P. 221°-223° C.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureThe reaction mixture is cooled in an ice bath
  3. filtrationthe solid filtered
  4. washwashed with ether
  5. customdried
  6. filtrationThe neutralized solid is filtered
  7. washwashed with water and isopropanol
  8. customdried
  9. additionis added
  10. concentrationThe resulting THF solution is concentrated
  11. temperaturecooled in an ice bath
  12. customresulting in the formation of a precipitate which
  13. filtrationis filtered
  14. washwashed with ether
  15. customdried in vacuo
  16. customtwice recrystallized from acetonitrile and isopropanol affording the desired product as the methane sulfonic salt, M.P. 221°-223° C.

Sources & evidence

ORD record
ord-3b425dc3ef864cde8592bc55be4a16fc
Source dataset
uspto-grants-1988_01
Patent number
US04721721

Reaction notes

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