Water → (3-Dimethylaminomethyl-phenyl)-thiourea

HRID 1861908Notes

Reaction equation

HRID 1861908 reaction equation
C(Cl)(=O)C1C=CC=CC=1.[S-:10][C:11]#[N:12].[NH4+].[NH2:14][C:15]1[CH:16]=[C:17]([CH2:21][N:22]([CH3:24])[CH3:23])[CH:18]=[CH:19][CH:20]=1.O>CC(C)=O>[NH:14]([C:15]1[CH:16]=[C:17]([CH2:21][N:22]([CH3:24])[CH3:23])[CH:18]=[CH:19][CH:20]=1)[C:11]([NH2:12])=[S:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 992943-amino-N,N-dimethylbenzylamine

Product 1

HCID 18621787(3-Dimethylaminomethyl-phenyl)-thioureaYield 35%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Benzoyl chloride (0.18 ml) was added to a solution of ammonium thiocyanate (0.12 g) in acetone (7 ml) and heated under reflux for 5 min. Subsequently, a solution of the compound (0.21 g) obtained in Example 38 in acetone (6 ml) was added. The reaction mixture was stirred at room temperature for 20 min and then water was added to give a yellow precipitate, which was separated off by filtration. To the recovered product, 10% aqueous sodium hydroxide solution (20 ml) was added and heated under reflux for 5 min. The reaction mixture was made acidic with 35% HCl, then weakly alkaline with 28% aqueous ammonia solution, and concentrated to 20 ml under reduced pressure. The resulting precipitate was filtered off and the filtrate was extracted with chloroform; the organic layer was dried with anhydrous magnesium sulfate and the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, chloroform methanol=5:1) to give 0.1 g of the titled compound (yield, 35%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 min
  3. customto give a yellow precipitate, which
  4. customwas separated off by filtration
  5. additionTo the recovered product, 10% aqueous sodium hydroxide solution (20 ml) was added
  6. temperatureheated
  7. temperatureunder reflux for 5 min
  8. concentrationconcentrated to 20 ml under reduced pressure
  9. filtrationThe resulting precipitate was filtered off
  10. extractionthe filtrate was extracted with chloroform
  11. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  12. concentrationthe solvent was concentrated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (eluent, chloroform methanol=5:1)

Sources & evidence

ORD record
ord-52d33028615e4f538db0da8524c8f47b
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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