Succinic anhydride → 3-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionic acid

HRID 273148ノート

反応式

HRID 273148 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][OH:8])=[NH:6].[C:12]1(=O)[O:17][C:15](=[O:16])[CH2:14][CH2:13]1>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:12]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[O:8][N:7]=2)[CH:9]=[CH:10][CH:11]=1

参加物

5

反応物 2

HCID 7922Succinic anhydrideHCID 178513296HCID 178513296、化合物

生成物 1

HCID 171222683-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionic acid収率 60%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-Chloro-N-hydroxy-benzamidine 4.52 g, 26.5 mmol) was heated with succinic anhydride (2.65 mg, 26.5 mmol) in DMF (5 ml) at 150° C. for an h. The reaction mixture was cooled down and diluted with ethyl acetate. The organic solution was washed with water and brine, concentrated by vacuum. The residue was triturated with 20% ethyl acetate in hexanes to give 4.0 g (60%) of 3-[3-(3-chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionic acid as white solid. ). 1H-NMR(CDCl3) d(ppm): 8.08 (s, 1H), 7.96 (d, 1H), 7.49 (d, 1H), 7.42 (t, 1H), 3.28 (t, 2H) and 3.04 (t, 2H). Step 2: 3-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionic acid hydrazide: This acid was reacted with iodoethane (1.6 g, 10.5 mmol) and K2CO3 (1.46 10.5 mmol) in DMF (5 ml) for 5 min to form 3-[3-(3-chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionic acid ethyl ester. The ethyl ester was then treated with 37% hydrazine (2 ml) in ethanol (5 ml) at 80° C. for 2 h to give 595 mg (65% in 3 steps) of 3-[3-(3-chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionic acid hydrazide as off-white solid 1H-NMR(CDCl3) d(ppm): 8.07 (s, 1H), 7.96 (d, 1H), 7.49 (d, 1H), 7.43 (t, 1H), 7.00 (w, 1H), 3.95 (w, 2H), 3.34 (t, 2H) and 2.79 (t, 2H).

後処理

  1. temperatureThe reaction mixture was cooled down
  2. washThe organic solution was washed with water and brine
  3. concentrationconcentrated by vacuum
  4. customThe residue was triturated with 20% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-c9c544d263ef4e829aaaf59db98a0e87
出典データセット
uspto-grants-2008_11
特許番号
US07456200B2

反応ノート

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