Ethyl orthoformate → HCID 15676106, compound

HRID 974049Notes

Reaction equation

HRID 974049 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:10]=2)[CH3:8])[O:4][N:3]=1.[CH:23](OCC)(OCC)OCC>>[CH3:23][NH:1][C:2]1[N:6]=[C:5]([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([OH:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:10]=2)[CH3:8])[O:4][N:3]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 156760943-Amino-5-(1-(3-benzoylphenyl)ethyl)-1,2,4-oxadiazole

Product 1

HCID 15676106HCID 15676106, compoundYield 48%

Procedure

To triethyl orthoformate (10 ml) was added 3-amino-5-(1-(3-benzoylphenyl)ethyl)-1,2,4-oxadiazole (0.30 g, 1.02 mmol). After reflux for 4.5 h, the mixture was evaporated under reduced pressure to a residue, which was extracted with dichloromethane after saturated NaHCO3 aq. was added. The extracts were washed with water, evaporated under reduced pressure to a residue, which was chromatographed to afford 3-methylamino-5-(1-(3-(α-hydroxybenzyl)phenyl)ethyl)-1,2,4-oxadiazole (0.15 g, 48% yield) as oily substance: NMR(CDCl3)δ 1.63(d, 3H), 2.82(d, 4H), 4.18(q, 1H), 4.20(m, 1H), 5.73(d, 1H), 7.33-7.42(m, 9H) ppm: IR(neat) 3430, 3330, 3040, 1600, 1490, 1450, 1340, 1320, 1150 cm-1.

Workup

  1. temperatureAfter reflux for 4.5 h
  2. customthe mixture was evaporated under reduced pressure to a residue, which
  3. extractionwas extracted with dichloromethane after saturated NaHCO3 aq.
  4. additionwas added
  5. washThe extracts were washed with water
  6. customevaporated under reduced pressure to a residue, which
  7. customwas chromatographed

Sources & evidence

ORD record
ord-8653427ec36e436caaf911910e55ac47
Source dataset
uspto-grants-1991_11
Patent number
US05066666

Reaction notes

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