Thioacetamide → 6-(2,5-Dimethyl-4-thiazolyl)-3,4-dihydro-2(1H)-quinolinone

HRID 2414106Notes

Reaction equation

HRID 2414106 reaction equation
Br[CH:2]([CH3:16])[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)=O.[C:17]([NH2:20])(=[S:19])[CH3:18]>C(O)C>[CH3:18][C:17]1[S:19][C:2]([CH3:16])=[C:3]([C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]3)[N:20]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 130510676-(2-Bromopropanoyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 140329866-(2,5-Dimethyl-4-thiazolyl)-3,4-dihydro-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-(α-bromopropionyl)-3,4-dihydrocarbostyril (7 g), thioacetamide (2 g) and absolute ethanol (250 ml) is stirred under reflux for 3 hours and allowed to cool overnight. The resulting white precipitate is filtered, washed with ether, dried and suspended in aqueous sodium bicarbonate for 30 minutes. The neutralized solid is filtered, washed with water, isopropanol, and recrystallized from isopropanol affording the desired product, M.P. 241°-242° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureto cool overnight
  3. filtrationThe resulting white precipitate is filtered
  4. washwashed with ether
  5. customdried
  6. filtrationThe neutralized solid is filtered
  7. washwashed with water, isopropanol
  8. customrecrystallized from isopropanol affording the desired product, M.P. 241°-242° C.

Sources & evidence

ORD record
ord-0472337085f04d84ad3b288017c70dc9
Source dataset
uspto-grants-1988_01
Patent number
US04721721

Reaction notes

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