Diethylamine → HCID 54478896, compound

HRID 1730037Notes

Reaction equation

HRID 1730037 reaction equation
C(O[C:4]([C:6]1[O:10][N:9]=[C:8]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:7]=1)=[O:5])C.[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22]>CO>[CH2:21]([N:23]([CH2:24][CH3:25])[C:4]([C:6]1[O:10][N:9]=[C:8]([CH:11]=[CH:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[N:7]=1)=[O:5])[CH3:22]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 54262228HCID 54262228, compound

Product 1

HCID 54478896HCID 54478896, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Ethoxycarbonyl-3-p-methoxystyryl-1,2,4-oxadiazole (1.25 g.) was suspended in dry methanol (5 ml.) and diethylamine (7.25 ml.) was added. The mixture was heated under reflux for 1 hour, when a solution was obtained. The solvent was removed under reduced pressure and the residual oil was dissolved in methanol and treated with charcoal. Evaporation of the filtrate left an oil, which was recrystallised from aqueous methanol to give the amide (1.199 g., 87.4%), m.p. 69°-70°, λmax. (EtOH) 225.5 300 (infl.) and 308 nm. (ε15400, 24400 and 25000), εmax. (CHBr3) 820 (C6H4), 970 (trans-CH=CH), 1650 (CO.N<),

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customwhen a solution was obtained
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe residual oil was dissolved in methanol
  6. additiontreated with charcoal
  7. customEvaporation of the filtrate
  8. waitleft an oil, which
  9. customwas recrystallised from aqueous methanol

Sources & evidence

ORD record
ord-a5b0659aded14ab8abb83a1e3b4d265f
Source dataset
uspto-grants-1976_11
Patent number
US03991067

Reaction notes

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