Hydrochloric Acid → N-(3-Methyl-5,6,7,8-tetrahydroquinolin-8-yl)thiourea

Reaction equation

C([NH:9][C:10]([NH:12][CH:13]1[C:22]2[N:21]=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH2:16][CH2:15][CH2:14]1)=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+].Cl>>[C:10]([NH:12][CH:13]1[C:22]2[N:21]=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH2:16][CH2:15][CH2:14]1)(=[S:11])[NH2:9]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 123582458-Benzoylthiocarbamoylamino-3-methyl-5,6,7,8-tetrahydroquinoline

Product 1

HCID 12358209N-(3-Methyl-5,6,7,8-tetrahydroquinolin-8-yl)thioureaYield 98%

Procedure

8-Benzoylthiocarbamoylamino-3-methyl-5,6,7,8-tetrahydroquinoline (6 g.) was treated with a 10% sodium hydroxide solution (24 ml.) and the mixture heated on a steam bath for 15 minutes. The cooled reaction mixture was adjusted to pH 1.0 with conc. HCl, filtered to remove benzoic acid and the filtrate adjusted to pH 10.0 with aqueous ammonia. The resultant solid was recrystallised from ethanol to give the hydrate of the title compound as colourless needles (4 g.). m.p. 114° C.