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

HRID 1646381Notes

Reaction equation

HRID 1646381 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8](C(=O)C)[C:7](=[O:15])[CH2:6][CH2:5]2.C([O:18][C:19]([NH:21][NH2:22])=[S:20])C.[C:23](#N)[CH3:24]>>[O:20]=[C:19]1[NH:21][N:22]=[C:24]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:15])[CH2:6][CH2:5]3)[CH2:23][S:18]1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 12567113O-Ethyl hydrazinecarbothioateHCID 67853249HCID 67853249, compound

Product 1

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

Procedure

To a solution of acetonitrile (100 ml) were added 6-chloro-acetyl-3,4-dihydro-2(1H)-quinolinone (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 yellow 6-(3,6-dihydro-2-oxo-2H-1,3,4-thiadiazin-5-yl)-3,4-dihydro-2(1H)-quinolinone (5.2 g), melting at 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-8181d7a915764b548379f0a1c2943b31
Source dataset
uspto-grants-1993_01
Patent number
US05179203

Reaction notes

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