Diisopropylethylamine → 3-(2,3-Dihydro-2-methylbenzofuran-7-yl)-5-(N-methoxy-N-methylamino)-1,3,4oxadiazol-2(3H)-one

HRID 1583754Notes

Reaction equation

HRID 1583754 reaction equation
Cl[C:2]([N:4]([C:12]1[C:20]2[O:19][CH:18]([CH3:21])[CH2:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)[NH:5][C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])=[O:3].C(N(C(C)C)CC)(C)C>CO>[CH3:21][CH:18]1[CH2:17][C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([N:4]3[N:5]=[C:6]([N:8]([O:10][CH3:11])[CH3:9])[O:7][C:2]3=[O:3])[C:20]=2[O:19]1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 13535829HCID 13535829, compound

Product 1

HCID 135358303-(2,3-Dihydro-2-methylbenzofuran-7-yl)-5-(N-methoxy-N-methylamino)-1,3,4oxadiazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.4 g of 1F, 2.5 g of N,N-diisopropyl-N-ethylamine and 75 ml of methanol were mixed. The resulting solution was allowed to stand at room temperature for 18 hours, then was warmed on a steam bath for 24 hours. The solvent was evaporated under reduced pressure and the residue was flash chromatographed over silica gel, a 2:15:33 v:v:v mixture of tetrahydrofuran, ethyl acetate and hexane being used as eluent. One product, Rf =0.14, was obtained as an off-white solid. Recrystallization from ether/hexane gave 2, m.p.: 91°-93° C. A second product, Rf =0.17, was obtained as an off-white solid. Recrystallization from ether/hexane gave 1, m.p.: 147°-149° C.

Workup

  1. temperaturewas warmed on a steam bath for 24 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customchromatographed over silica gel
  4. additiona 2:15:33 v:v:v mixture of tetrahydrofuran, ethyl acetate and hexane being
  5. customOne product, Rf =0.14, was obtained as an off-white solid
  6. customRecrystallization from ether/hexane
  7. customgave 2, m.p.: 91°-93° C
  8. customA second product, Rf =0.17, was obtained as an off-white solid
  9. customRecrystallization from ether/hexane
  10. customgave 1, m.p.: 147°-149° C.

Sources & evidence

ORD record
ord-bf0c263d745f4c04a3c53fa31e7de336
Source dataset
uspto-grants-1985_11
Patent number
US04554283

Reaction notes

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