Sodium hydride → 5-(4-Iodophenyl)-3-methyl-1,2,4-oxadiazole

HRID 2294972Notes

Reaction equation

Cl.[C:2](=[N:5][OH:6])([NH2:4])[CH3:3].[H-].[Na+].[I:9][C:10]1[CH:20]=[CH:19][C:13]([C:14](OCC)=O)=[CH:12][CH:11]=1>O1CCCC1>[CH3:3][C:2]1[N:4]=[C:14]([C:13]2[CH:19]=[CH:20][C:10]([I:9])=[CH:11][CH:12]=2)[O:6][N:5]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Acetamidoxime hydrochloride (1.5 g) was added portionwise to an ice-cooled suspension of sodium hydride (1.18 g of a 60% dispersion in oil) in dry tetrahydrofuran (40 ml) under an atmosphere of argon. Molecular sieves (type 4A, 8-12 mesh) were added to the reaction mixture, followed by a solution of ethyl 4-iodobenzoate (3.73 g) in tetrahydrofuran (10 ml). The reaction mixture was heated at 65° C. for 3 hours. The reaction mixture was allowed to cool to ambient temperature and was then partitioned between ethyl acetate and water. The organic phase was separated, washed with saturated brine, dried (MgSO4) and evaporated. The residue was purified by flash column chromatography on silica gel using a 70:30 (v/v) mixture of ethyl acetate/hexane as eluent to give 3-methyl-5-(4-iodophenyl)-1,2,4-oxadiazole (1.12 g) as a solid, m.p. 136°-137° C.; microanalysis, found: C, 38.2; H, 2.5; N, 9.5%; C9H7IN2O requires: C, 37.8; H, 2.47; N, 9.79%; NMR: 2.41(3H,s), 7.84(2H,d), 8.02(2H,d); m/z 287(M+H).

Workup

temperaturecooled
temperatureto cool to ambient temperature
customwas then partitioned between ethyl acetate and water
customThe organic phase was separated
washwashed with saturated brine
dry with materialdried (MgSO4)
customevaporated
customThe residue was purified by flash column chromatography on silica gel using
additiona 70:30 (v/v) mixture of ethyl acetate/hexane as eluent

Sources & evidence

ORD record: ord-2b90760b7ea84241bbb2827aec56cf68
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05691349

Reaction notes

Loading…