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

HRID 596450Notes

Reaction equation

HRID 596450 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-5da23d86839e4bc9be3bd51fe207d3fb
Source dataset
uspto-grants-1977_03
Patent number
US04011229

Reaction notes

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