Potassium Carbonate → [3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

HRID 2063684Notes

Reaction equation

HRID 2063684 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:15])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.C([N:24]=[C:25]=[S:26])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:25]([NH2:24])=[S:26])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline

Product 1

HCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine (500 mg, 2.46 mmol) in THF (30 ml) at 0° C. was slowly added benzoyl isothiocyanate (0.366 ml, 2.583 mmol) and the reaction mixture was stirred at rt for 2 hours. The solvents were evaporated and the residue was dissolved in methanol (50 ml). A solution of potassium carbonate (1.02 g, 7.38 mmol) in water (23 ml) was added dropwise at rt, the reaction mixture was stirred for 3 h at rt. The methanol was evaporated, water (10 ml) was added and stirred at rt for 1 hour. The solids were filtered off, washed with diethyl ether and dried in vacuo. After trituration with diethyl ether the title compound was obtained as light yellow solid (490 mg, 76%). MS ISP (m/e): 263.1 (100) [(M+H)+].

Workup

  1. customat 0° C.
  2. customThe solvents were evaporated
  3. dissolutionthe residue was dissolved in methanol (50 ml)
  4. stirringthe reaction mixture was stirred for 3 h at rt
  5. customThe methanol was evaporated
  6. additionwater (10 ml) was added
  7. stirringstirred at rt for 1 hour
  8. filtrationThe solids were filtered off
  9. washwashed with diethyl ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-ff728a72183e486d9e17d771a26545dc
Source dataset
uspto-grants-2012_10
Patent number
US08288403B2

Reaction notes

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