5-(Chloromethyl)-2-methoxybenzonitrile → 5-[[[5-(2,3-Dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]thio]methyl]-2-methoxybenzonitrile

HRID 452701Notes

Reaction equation

HRID 452701 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:14][C:13]([SH:15])=[N:12][N:11]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.Cl[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:26][CH3:27])=[C:22]([CH:25]=1)[C:23]#[N:24]>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:14][C:13]([S:15][CH2:17][C:18]4[CH:19]=[CH:20][C:21]([O:26][CH3:27])=[C:22]([CH:25]=4)[C:23]#[N:24])=[N:12][N:11]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 229961915-(Chloromethyl)-2-methoxybenzonitrileHCID 178527934HCID 178527934, compound

Product 1

HCID 445903785-[[[5-(2,3-Dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]thio]methyl]-2-methoxybenzonitrileYield 72%

Procedure

In the same manner as in Example 1 and using 5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazole-2-thiol instead of 5-(benzothiazol-6-yl)-1,3,4-oxadiazole-2-thiol and 5-(chloromethyl)-2-methoxybenzonitrile instead of 3-(trifluoromethyl)benzyl chloride, the title compound (yield 72%) was obtained as colorless crystals.

Sources & evidence

ORD record
ord-08ba2513e68d48b0a7883542b54b2bca
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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