2-Aminophenol → N-(4-(3-methylpyridin-2-yloxy)phenyl)benzo[d]oxazol-2-amine

HRID 1880045Notes

Reaction equation

[N:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:6][CH:5]=1)=[C:2]=S.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25].C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[CH3:15][C:14]1[C:9]([O:8][C:7]2[CH:16]=[CH:17][C:4]([NH:1][C:2]3[O:25][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=3)=[CH:5][CH:6]=2)=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 75 °C

Procedure

The mixture of 2-(4-isothiocyanatophenoxy)-3-methylpyridine (136 mg, 0.56 mmol), 2-aminophenol (74 mg, 0.67 mmol), and N,N′-dicyclohexylcarbodiimide (174 mg, 0.84 mmol) in THF (5 mL) was heated at 75° C. for 16 h. The solvent was evaporated and the crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of 0% to 30% EtOAc in hexane, to provide N-(4-(3-methylpyridin-2-yloxy)phenyl)benzo[d]oxazol-2-amine as white solid. MS (ESI, pos. ion) m/z: 318.1 (M+1).

Workup

customThe solvent was evaporated
customthe crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (40 g)
washeluting with a gradient of 0% to 30% EtOAc in hexane

Sources & evidence

ORD record: ord-6a9e1e3954924bba911674b90824ce83
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318718B2

Reaction notes

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