2-Methoxyaniline → Urea, 1-(o-methoxyphenyl)-2-thio-

HRID 21681Notes

Reaction equation

HRID 21681 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.C([N:18]=[C:19]=[S:20])(=O)C1C=CC=CC=1>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:19]([NH2:18])=[S:20]

Participants

4

Reactant 2

HCID 70002-MethoxyanilineHCID 68284Benzoyl isothiocyanate

Product 1

HCID 722774Urea, 1-(o-methoxyphenyl)-2-thio-Yield 57.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 50 ml of acetone were added 2.46 g of o-anisidine and 3.75 g of benzoyl isothiocyanate, and the mixture is stirred under reflux for 2 hours and, then, allowed to stand overnight in a refrigerator at 5° C. The resulting crystals were collected by filtration, washed with cold acetone and dried under reduced pressure. The crystals were added to 50 ml of 30% methylamine-methanol and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated to dryness under reduced pressure, and the residue was washed with ethanol-ethyl acetate and dried under reduced pressure. The procedure provided 2.08 g of N-(o-methoxyphenyl)thiourea.

Workup

  1. temperatureunder reflux for 2 hours
  2. filtrationThe resulting crystals were collected by filtration
  3. washwashed with cold acetone
  4. customdried under reduced pressure
  5. additionThe crystals were added to 50 ml of 30% methylamine-methanol
  6. stirringthe mixture was stirred at room temperature overnight
  7. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  8. washthe residue was washed with ethanol-ethyl acetate
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-de9bab9b5e424189ac8c17363b982488
Source dataset
uspto-grants-1995_06
Patent number
US05424431

Reaction notes

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