Sodium Hydroxide → 1-(4-Bromo-3,5-dimethylphenyl)thiourea

HRID 1754983Notes

Reaction equation

HRID 1754983 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH2:9])=[CH:4][C:3]=1[CH3:10].C([N:19]=[C:20]=[S:21])(=O)C1C=CC=CC=1.[OH-].[Na+]>CC(C)=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:20]([NH2:19])=[S:21])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 68284Benzoyl isothiocyanateHCID 123831174-Bromo-3,5-dimethylaniline

Product 1

HCID 508805361-(4-Bromo-3,5-dimethylphenyl)thioureaYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-bromo-3,5-dimethyl-phenylamine (200 mg) and benzoyl isothiocyanate (0.14 ml) in acetone (2 ml) was heated under reflux for 30 minutes. After cooling the reaction solution, a 1 N aqueous sodium hydroxide solution (2.19 ml) was added and the mixture was stirred at 50° C. for 12 hours. The mixture was extracted with dichloromethane, and the organic layer was then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was triturated with hexane to give (4-bromo-3,5-dimethyl-phenyl)-thiourea (146 mg, 57%).

Workup

  1. temperatureunder reflux for 30 minutes
  2. temperatureAfter cooling the reaction solution
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialthe organic layer was then dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was triturated with hexane

Sources & evidence

ORD record
ord-f5caee973b464469b053c447a6aa5866
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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