Methyl isothiocyanate → 8-Methylthiocarbamoylamino-3-methyl-5,6,7,8-tetrahydroquinoline

HRID 1730010Notes

Reaction equation

HRID 1730010 reaction equation
Cl.Cl.[NH2:3][CH:4]1[C:13]2[N:12]=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[CH2:7][CH2:6][CH2:5]1.[CH3:15][N:16]=[C:17]=[S:18]>C(#N)C>[CH3:15][NH:16][C:17]([NH:3][CH:4]1[C:13]2[N:12]=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[CH2:7][CH2:6][CH2:5]1)=[S:18]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 123582218-Amino-3-methyl-5,6,7,8-tetrahydroquinoline dihydrochloride

Product 1

HCID 123582118-Methylthiocarbamoylamino-3-methyl-5,6,7,8-tetrahydroquinolineYield 99.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 8-amino product of Example 3 (free base) (3 g.) was dissolved in acetonitrile (30 ml.) and the solution treated with methylisothiocynate (1.35 g.) and heated at reflux for 2 hours. The solvent was removed in Vacuo and the residual solid recrystallised from absolute ethanol to give the title compound as colourless needles (3 g.) m.p. 113° C. (Found: C,61.4; H,7.3; N, 17.8. C12H17N3S requires : C, 61.2; H, 7.3; N, 17.9L%). The product displayed anti-ulcer, antisecretory and Gastric anti-histamine activity.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was removed in Vacuo
  4. customthe residual solid recrystallised from absolute ethanol

Sources & evidence

ORD record
ord-c60cd7929125439480584aba65935035
Source dataset
uspto-grants-1976_11
Patent number
US03991065

Reaction notes

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