Ethanol → [4-(2-Phenyl-2-o-tolyl-vinyl)-pyridin-2-yl]-urea

HRID 1023438Notes

Reaction equation

[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[CH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]([N:31]=C=O)(=[O:30])C1C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[CH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:23]([NH2:31])=[O:30])[CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The crude 4-(2-phenyl-2-o-tolyl-vinyl)-pyridin-2-ylamine (251 mg) is dissolved in methylene chloride (5 mL). Then benzoyl isocynate (258 mg, 1.75 mmol) is added. The reaction mixture is sealed and heated at 50° C. for 16 hour. The solvent is then carefully removed and to the residue are added ethanol (5 mL) and potassium carbonate (182 mg, 1.32 mmol). The resulting mixture is heated at 80° C. for 45 min. Then solvent is removed and the residue is partitioned between water (45 mL) and EtOAc (55 mL). The aqueous layer is separated and extracted with EtOAc (2×30 mL). The organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) affords 185 mg of the desired product.

Workup

customThe reaction mixture is sealed
customThe solvent is then carefully removed and to the residue
temperatureThe resulting mixture is heated at 80° C. for 45 min
customThen solvent is removed
customthe residue is partitioned between water (45 mL) and EtOAc (55 mL)
customThe aqueous layer is separated
extractionextracted with EtOAc (2×30 mL)
concentrationconcentrated
customto give the crude product
customPurification by silica flash column chromatography

Sources & evidence

ORD record: ord-ff7a81728e26460da7138b3dd27900a8
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722709B2

Reaction notes

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