Sodium Hydroxide → N-(3-Methyl-5,6,7,8-tetrahydroquinolin-8-yl)thiourea

HRID 1730012Notes

Reaction equation

HRID 1730012 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+]>>[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

3

Reactant 2

HCID 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. HC1, 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. (Found C, 55.3; H, 7.3; N, 17.2. C11H15N3S.H2O requires: C,55.1; H, 7.3; N, 17.4%). The product displayed anti-ulcer activity.

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-f72d29f1742b477d8b14cf3f349fd000
Source dataset
uspto-grants-1976_11
Patent number
US03991065

Reaction notes

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