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

HRID 273148노트

반응식

HRID 273148 반응식
[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

참가 물질

5

반응물 2

HCID 7922Succinic anhydrideHCID 178513296HCID 178513296, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c9c544d263ef4e829aaaf59db98a0e87
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456200B2

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