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

HRID 861412Notes

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 sieve type 4A (8-12 mesh) were added followed by a solution of ethyl 4-iodobenzoate (3.73 g) in tetrahydrofuran (10 ml). The mixture was heated at 65° C. for 3 hours. The mixture was cooled to ambient temperature and partitioned between ethyl acetate and water. The organic extract was separated, washed with saturated brine, dried (MgSO4) and evaporated. The residue was purified by flash column chromatgraphy 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 as a solid (1.12 g), m.p. 136°-7° C.; microanalysis, found: C, 38.2; H, 2.5; H, 9.5%; C9H7IN2O requires: C, 37.8; H, 2.47; N, 9.79%; NMR: 2.41(3H,s), 7.84(2H,d) and 8.02(2H,d); m/z 287(M+H).

Workup

temperaturecooled
temperatureThe mixture was cooled to ambient temperature
custompartitioned between ethyl acetate and water
extractionThe organic extract
customwas separated
washwashed with saturated brine
dry with materialdried (MgSO4)
customevaporated
customThe residue was purified by flash column chromatgraphy on silica gel using
additiona 70:30 (v/v) mixture of ethyl acetate/hexane as eluent

Sources & evidence

ORD record: ord-5a126ab861f34fcc8a6f87756aad198a
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05714496

Reaction notes

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