Potassium Carbonate → [4-(2,4-Dimethyl-thiazol-5-yl)-3-methoxy-phenyl]-thiourea

HRID 2076132Notes

Reaction equation

HRID 2076132 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=2[O:15][CH3:16])=[C:5]([CH3:7])[N:6]=1.C([N:25]=[C:26]=[S:27])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[CH3:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:26]([NH2:25])=[S:27])=[CH:10][C:9]=2[O:15][CH3:16])=[C:5]([CH3:7])[N:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 670962794-(2,4-Dimethyl-thiazol-5-yl)-3-methoxy-phenylamine

Product 1

HCID 86632613[4-(2,4-Dimethyl-thiazol-5-yl)-3-methoxy-phenyl]-thioureaYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2,4-dimethyl-thiazol-5-yl)-3-methoxy-phenylamine (100 mg, 0.43 mmol) in tetrahydrofurane (4 mL) was added drop wise under stirring and under an atmosphere benzoyl isothiocyanate (63.6 ul, 0.45 mmol). The reaction was stirred at room temperature for 3 hours and the solvent was removed under reduced pressure. The residue was dissolved in methanol (6 mL) and a solution of potassium carbonate (177 mg, 1.28 mmol) in water (3 mL) was added. The resulting suspension was stirred at room temperature over night. The precipitate was filtered off, washed with water and diethyl ether to yield the title compound as a pale yellow solid (90 mg, 72%). MS ISP (m/e): 294.1 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=9.81 (s, 1H, NH), 7.35 (s, 1H), 7.21 (d, 1H), 7.01 (s, 1H), 3.76 (s, 3H), 2.59 (s, 3H), 2.20 (s, 3H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (6 mL)
  3. stirringThe resulting suspension was stirred at room temperature over night
  4. filtrationThe precipitate was filtered off
  5. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-656f13b391fd440287ce02bbbc1b0f20
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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