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

HRID 596451Notes

Reaction equation

HRID 596451 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-5a997140f8774b28b767f70e4571d26d
Source dataset
uspto-grants-1977_03
Patent number
US04011229

Reaction notes

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