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

HRID 1583756노트

반응식

HRID 1583756 반응식
[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

참가 물질

4

반응물 2

HCID 81531DiisopropylethylamineHCID 13535833HCID 13535833, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-83cce786075840d9a41a9854b1b39dee
출처 데이터셋
uspto-grants-1985_11
특허 번호
US04554283

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