Benzoyl isothiocyanate → 8-Benzoylthiocarbamoylamino-3-methyl-5,6,7,8-tetrahydroquinoline

HRID 1730011Notes

Reaction equation

HRID 1730011 reaction equation
[NH2:1][CH:2]1[C:11]2[N:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[C:13]([N:21]=[C:22]=[S:23])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC(C)=O>[C:13]([NH:21][C:22]([NH:1][CH:2]1[C:11]2[N:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1)=[S:23])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 123582203-Methyl-5,6,7,8-tetrahydroquinolin-8-amine

Product 1

HCID 123582458-Benzoylthiocarbamoylamino-3-methyl-5,6,7,8-tetrahydroquinolineYield 12.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 8-amino-3-methyl-5,6,7,8-tetrahydroquinoline (6. g.) in acetone (48 ml.) was treated with benzoylisothiocyanate (6 g.) and the mixture heated at reflux for 45 minutes. The solvent was removed in vacuo and the residual solid recrystallised from ethanol-ether to give the title compound as colourless needles (7.2 g.) m.p. 168° C. (Found; C,66.5; H, 6.1; N, 13.0 C18H19N3OS requires: C, 66.4; H, 5.9; N, 12.9%).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 45 minutes
  3. customThe solvent was removed in vacuo
  4. customthe residual solid recrystallised from ethanol-ether

Sources & evidence

ORD record
ord-cd311a248a8d4ef393b4aaca0861842a
Source dataset
uspto-grants-1976_11
Patent number
US03991065

Reaction notes

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