Thiourea → 105316-79-8

HRID 2414104Notes

Reaction equation

HRID 2414104 reaction equation
Cl[CH2:2][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.[NH2:16][C:17]([NH2:19])=[S:18]>C(O)C>[NH2:19][C:17]1[S:18][CH:2]=[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:16]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 49617906-(2-Chloroacetyl)-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 725400105316-79-8

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-(Chloroacetyl)-3,4-dihydrocarbostyril (7 g), thiourea (2.6 g) and absolute ethanol (250 ml) is stirred under reflux for two hours, cooled in an ice bath, filtered, and the filtered solid washed with ether and dried. The solid is suspended in aqueous sodium bicarbonate and stirred for 30 minutes, filtered, washed with isopropanol, dried and refluxed in methanol (300 ml) overnight. The resulting solid is filtered, suspended in boiling methanol (300 ml) and methane sulfonic acid (2.8 ml) added, resulting in the formation of a precipitate which is filtered, twice recrystallized from ethanol/DMF affording the desired product as the methane sulfonic acid salt, M.P. >250° C.

Workup

  1. temperatureunder reflux for two hours
  2. temperaturecooled in an ice bath
  3. filtrationfiltered
  4. washthe filtered solid washed with ether
  5. customdried
  6. filtrationfiltered
  7. washwashed with isopropanol
  8. customdried
  9. temperaturerefluxed in methanol (300 ml) overnight
  10. filtrationThe resulting solid is filtered
  11. additionadded
  12. customresulting in the formation of a precipitate which
  13. filtrationis filtered
  14. customtwice recrystallized from ethanol/DMF affording the desired product as the methane sulfonic acid salt, M.P. >250° C.

Sources & evidence

ORD record
ord-b370d7bc72b54d32a7215c2fc3151221
Source dataset
uspto-grants-1988_01
Patent number
US04721721

Reaction notes

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