6-(2-Chloroacetyl)-1,2,3,4-tetrahydroquinolin-2-one → 6-(3,6-Dihydro-2-oxo-2H-1,3,4-thiadiazin-5-yl)-3,4-dihydro-2(1H)-quinolinone

HRID 2118482Notes

Reaction equation

HRID 2118482 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.C([O:18][C:19]([NH:21][NH2:22])=[S:20])C>C(#N)C>[NH:11]1[C:12]2[C:7](=[CH:6][C:5]([C:3]3[CH2:2][S:20][C:19](=[O:18])[NH:21][N:22]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:9][C:10]1=[O:15]

Participants

4

Reactant 2

HCID 49617906-(2-Chloroacetyl)-1,2,3,4-tetrahydroquinolin-2-oneHCID 12567113O-Ethyl hydrazinecarbothioate

Product 1

HCID 54871436-(3,6-Dihydro-2-oxo-2H-1,3,4-thiadiazin-5-yl)-3,4-dihydro-2(1H)-quinolinoneYield 66.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of acetonitrile (100 ml) were added 6-chloroacetyl-3,4-dihydrocarbostyril (6.7 g) and ethoxythiocarbonylhydrazine (5.4 g) and the mixture was stirred for 2 hours, cooled and then filtered off. The filtrate was recrystallized from dimethylformamide (30 ml) and water (10 ml) to obtain pale yellowish 5-(3,4-dihydrocarbostyril-6-yl)-3,6-dihydro-1,3,4-thiadiazin-2-one (5.2 g), m.p. 271°-272° C. (decomposition).

Workup

  1. temperaturecooled
  2. filtrationfiltered off
  3. customThe filtrate was recrystallized from dimethylformamide (30 ml) and water (10 ml)

Sources & evidence

ORD record
ord-6e351a474c884dbb83fee8cdbf5cfc60
Source dataset
uspto-grants-1987_07
Patent number
US04678785

Reaction notes

Loading…