Toluene → 5-(p-Methoxyphenyl)acetyl-3-(3-nitrophenyl)-1,2,4-oxadiazole

HRID 916242노트

반응식

HRID 916242 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7](=[N:9][OH:10])[NH2:8])([O-:3])=[O:2].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](=[O:29])[CH2:24]C(OC)=O)=[CH:18][CH:17]=1.C1(C)C=CC=CC=1>CCCCCCC>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([C:24]2[O:10][N:9]=[C:7]([C:6]3[CH:11]=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[N:8]=2)=[O:29])=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 1140TolueneHCID 3781554N'-hydroxy-3-nitrobenzenecarboximidamideHCID 26596824Methyl 4-(4-methoxyphenyl)-3-oxobutanoate

생성물 1

HCID 694258215-(p-Methoxyphenyl)acetyl-3-(3-nitrophenyl)-1,2,4-oxadiazole수율 89.7%

시약·촉매·용매 1

HCID 8900Heptane용매

실험 절차

In a 100 ml flask, place 5 g (0.0276 m) of 3-nitrobenzamidoxime (9a), 8.6 g (0.0414 m) of methyl p-methoxyphenyacetoacetate (10c; R1=p-methoxyphenyl), and 50 ml of toluene. Heat and stir the reaction mixture under reflux with a Dean-Stark trap for 14 hrs. Cool the reaction mixture to room temperature, add 40 ml of heptane and stir for 30 min. Collect solid, wash with heptane, and dry in air to give 8.4 g (85%) of 5-(p-methoxyphenyl)acetyl-3-(3-nitrophenyl)-1,2,4-oxadiazole [Formula II: R1=p-methoxyphenyl and R2=3-nitrophenyl].

후처리

  1. temperatureHeat
  2. temperatureunder reflux with a Dean-Stark trap for 14 hrs
  3. stirringstir for 30 min
  4. customCollect solid
  5. washwash with heptane
  6. customdry in air

출처 및 근거

ORD 기록
ord-31e49f47323e43ba9bfe1c8fd6177b5f
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268235B2

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