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

HRID 1583756ノート

反応式

HRID 1583756 の反応式
[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

参加物

4

反応物 2

HCID 81531DiisopropylethylamineHCID 13535833HCID 13535833、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-83cce786075840d9a41a9854b1b39dee
出典データセット
uspto-grants-1985_11
特許番号
US04554283

反応ノート

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