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

HRID 2071599Notes

Reaction equation

HRID 2071599 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 60.2%

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.

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-5f24109214d441319147838a86e4065a
Source dataset
uspto-grants-1977_09
Patent number
US04048175

Reaction notes

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