2-Chloronicotinonitrile → 2-({4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyl}oxy)nicotinonitrile

HRID 1294231Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=1.Cl[C:24]1[C:29]([C:30]#[N:31])=[CH:28][CH:27]=[CH:26][N:25]=1>CN(C)C=O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][O:22][C:24]2[N:25]=[CH:26][CH:27]=[CH:28][C:29]=2[C:30]#[N:31])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 25 °C

Procedure

(4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]phenyl)methanol (400 g) and then 2-chloro-3-cyanopyridine (206.7 g) were added to dimethylformamide (1.6 L). To the obtained mixture was added triturated sodium hydroxide (59.4 g) and the mixture was stirred at 20-30° C. for 48 hrs. Water (1.6 L) was dropwise added at the same temperature and the mixture was stirred for 2 hrs. The precipitated crystals were collected by filtration, washed with water (1.6 L) and then ice-cooled ethyl acetate (800 ml), and dried (40° C.) under reduced pressure to give 2-({4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyl}oxy)nicotinonitrile as white crystals.

Workup

additionTo the obtained mixture was added
customtriturated sodium hydroxide (59.4 g)
additionWater (1.6 L) was dropwise added at the same temperature
stirringthe mixture was stirred for 2 hrs
filtrationThe precipitated crystals were collected by filtration
washwashed with water (1.6 L)
temperatureice-cooled ethyl acetate (800 ml)
customdried (40° C.) under reduced pressure

Sources & evidence

ORD record: ord-7e1ac9d9ab3548bda14b03fe9467b116
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238716B2

Reaction notes

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