3-Nitrobenzaldehyde → 1,4-dihydro-2,6-dimethyl-3,5-di-[3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazol-5-yl]-4-(3-nitrophenyl)pyridine

HRID 247124Notes

Reaction equation

[CH2:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10][N:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:12])[N:6]=1)[C:2]([CH3:4])=O.[N+:20]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=O)([O-:22])=[O:21].[OH2:31].[NH3:32]>C(O)(C)C>[CH3:4][C:2]1[NH:32][C:2]([CH3:4])=[C:1]([C:5]2[O:31][N:8]=[C:7]([CH2:10][N:11]([CH3:12])[CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:6]=2)[CH:26]([C:25]2[CH:28]=[CH:29][CH:30]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=2)[C:1]=1[C:5]1[O:9][N:8]=[C:7]([CH2:10][N:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:12])[N:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 520 mg of 5-acetonyl-3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazole, 150 mg of 3-nitrobenzaldehyde, 3 ml of isopropyl alcohol and 70 mg of 29% ammonia water in an autoclave was heated at 100° C. in an oil bath for 15 hours. After cooling, the mixture was evaporated in vacuo and the residue was chromatographed on silica gel using chloroform-methanol (30:1) as eluent to give 1,4-dihydro-2,6-dimethyl-3,5-di-[3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazol-5-yl]-4-(3-nitrophenyl)pyridine, IR νmaxneat cm-1 : 3300, 3000, 1655, 1525, 1490, 1450, 1350.

Workup

temperatureAfter cooling
customthe mixture was evaporated in vacuo
customthe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-e38b39043af44e77bb99f8430ffdfad2
Source dataset: uspto-grants-1987_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04705786

Reaction notes

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