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

HRID 916242ノート

反応式

HRID 916242 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8900Heptane溶媒

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-31e49f47323e43ba9bfe1c8fd6177b5f
出典データセット
uspto-grants-2007_09
特許番号
US07268235B2

反応ノート

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