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

HRID 1583756Notes

Reaction equation

HRID 1583756 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:6][C:5]2[C:7]([CH3:21])=[CH:8][CH:9]=[C:10]([N:11]3[N:15]=[C:14]([N:16](OC)[CH3:17])[O:13][C:12]3=[O:20])[C:4]=2[O:3]1.C(N(C(C)C)CC)(C)C>CO>[CH3:1][C:2]1([CH3:22])[CH2:6][C:5]2[C:7]([CH3:21])=[CH:8][CH:9]=[C:10]([N:11]3[N:15]=[C:14]([NH:16][CH3:17])[O:13][C:12]3=[O:20])[C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 13535833HCID 13535833, compound

Product 1

HCID 135358343-(2,3-Dihydro-2,2,4-trimethylbenzofuran-7-yl)-5-(methylamino)-1,3,4-oxadiazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.0 g of 3, 75 ml of methanol and 1.3 g of N,N-diisopropyl-N-ethylamine was warmed on a steam bath for 18 hours. The solvent was evaporated under reduced pressure, the residue was mixed with 75 ml of water and the mixture was extracted with ether. The extract was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was flash-chromatographed over silica gel, using a 2:15:33 v:v:v mixture of THF, ethyl acetate and hexane as eluent. Two products were obtained: one, a light amber syrup, Rf=0.49, was identified as 3; the second, a solid (Rf=0.24) was recrystallized from ether to give 4, as a colorless solid, m.p.: 183°-184° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was mixed with 75 ml of water
  3. extractionthe mixture was extracted with ether
  4. dry with materialThe extract was dried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was flash-chromatographed over silica gel
  7. additionv:v mixture of THF, ethyl acetate and hexane as eluent
  8. customTwo products were obtained
  9. customthe second, a solid (Rf=0.24) was recrystallized from ether
  10. customto give 4

Sources & evidence

ORD record
ord-83cce786075840d9a41a9854b1b39dee
Source dataset
uspto-grants-1985_11
Patent number
US04554283

Reaction notes

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