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

HRID 2071600Notes

Reaction equation

HRID 2071600 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

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 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.

Workup

  1. temperaturethe mixture heated on a steam bath for 15 minutes
  2. customThe cooled reaction mixture
  3. filtrationfiltered
  4. customto remove benzoic acid
  5. customThe resultant solid was recrystallised from ethanol

Sources & evidence

ORD record
ord-0e8edd332dfc49ca8f6f80a3d862fdc0
Source dataset
uspto-grants-1977_09
Patent number
US04048175

Reaction notes

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