Diethylamine → HCID 86734158, compound

HRID 1730038Notes

Reaction equation

HRID 1730038 reaction equation
C(O[C:4]([C:6]1[O:10][N:9]=[C:8](/[CH:11]=[CH:12]/[C:13]2[O:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)[N:7]=1)=[O:5])C.[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22]>>[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[O:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)[N:7]=1)=[O:5])[CH3:22]

Participants

3

Reactant 2

HCID 8021DiethylamineHCID 86734159HCID 86734159, compound

Product 1

HCID 86734158HCID 86734158, compoundYield 57%

Procedure

trans-5-Ethoxycarbonyl-3-(5-nitrofur-2-ylvinyl)-1,2,4-oxadiazole (332 mg.) was heated under reflux with diethylamine (5 ml.) for 30 min. to give a deep red solution. Evaporation gave a red solid; recrystallisation from methanol (3 ml.) gave trans-5-diethylcarbamoyl-3-(5-nitrofur-2-ylvinyl)1,2,4-oxadiazole (208 mg., 57%), m.p. 118°-119°, λmax. (EtOH) 240 and 349 nm. (ε18,600 and 19,900), νmax. (CHBr3) 1665 (CONEt2), 1510, 1352 (NO2) and 960 cm.-1 (trans CH=CH).

Workup

  1. customto give a deep red solution
  2. customEvaporation
  3. customgave a red solid
  4. customrecrystallisation from methanol (3 ml.)

Sources & evidence

ORD record
ord-ec6555b51a19413493ca42e7d9043b00
Source dataset
uspto-grants-1976_11
Patent number
US03991067

Reaction notes

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