Potassium Carbonate → N-(4-Chloro-3-methoxyphenyl)thiourea

HRID 2222204Notes

Reaction equation

HRID 2222204 reaction equation
C([N:9]=[C:10]=[S:11])(=O)C1C=CC=CC=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:14]=1[O:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:10]([NH2:9])=[S:11])=[CH:15][C:14]=1[O:20][CH3:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 131036924-Chloro-3-methoxyaniline

Product 1

HCID 86056613N-(4-Chloro-3-methoxyphenyl)thiourea

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzoyl isothiocyanate (8.8 mL, 64 mmol) was added dropwise to a solution of 4-chloro-3-methoxy-benzenamine (10 g, 63 mmol) in 160 mL THF. The mixture was stirred at room temperature for 40 minutes, volatiles were removed and the residue was dissolved in 400 mL methanol. A solution of potassium carbonate (26.3 g, 190 mmol) in 200 mL water was added and the mixture was stirred at room temperature for 90 minutes. The tide product (13.5 g, 98%) precipitated after removal of 450 mL of the solvents.

Workup

  1. customvolatiles were removed
  2. dissolutionthe residue was dissolved in 400 mL methanol
  3. stirringthe mixture was stirred at room temperature for 90 minutes
  4. customThe tide product (13.5 g, 98%) precipitated
  5. customafter removal of 450 mL of the solvents

Sources & evidence

ORD record
ord-ee771198a5c541a5898aea2bfc0202a7
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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