3-(2-Nitrophenyl)-2-oxopropanoic acid → 2-[[4-(3,4-Dichlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]-3-(2-nitrophenyl)propanoic acid

HRID 2380755

반응식

HRID 2380755 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11](=O)[C:12]([OH:14])=[O:13])([O-:3])=[O:2].[Cl:16][C:17]1[CH:18]=[C:19]([C:24]2[N:25]=[C:26]([NH:29][NH2:30])[S:27][CH:28]=2)[CH:20]=[CH:21][C:22]=1[Cl:23]>C(O)(=O)C.C(O)C>[Cl:16][C:17]1[CH:18]=[C:19]([C:24]2[N:25]=[C:26]([NH:29][N:30]=[C:11]([CH2:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])[C:12]([OH:14])=[O:13])[S:27][CH:28]=2)[CH:20]=[CH:21][C:22]=1[Cl:23]

참가 물질

5

반응물 2

HCID 795833-(2-Nitrophenyl)-2-oxopropanoic acidHCID 71740714-(3,4-Dichlorophenyl)-2-hydrazinylthiazole

생성물 1

HCID 28310242-[[4-(3,4-Dichlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]-3-(2-nitrophenyl)propanoic acid

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

3-(2-Nitro-phenyl)-2-oxo-propionic acid (1.0 mmol, 209 mg) in 5% acetic acid (2 mL) was added in to solution of 4-(3,4-dichloro-phenyl)-thiazol-2-yl-hydrazine (1.0 mmol, 259 mg) in ethanol (4 mL). The reaction mixture was stirred at 90° C. for 1 h and cooled to 0° C.; the orange solid was precipitated, filtered and washed by water. Recrystallization from MeOH—H2O afford the final product as a yellow power (600 mg, 66.7%). mp; Z/E isomer was further separated by HPLC-MS, using gradient eluting solvents: 0.05% HOAc in acetonitrile 50% : 0.05% HOAc in water 50% to 0.05% HOAc in acetonitrile 75%: 0.05% HOAc in water 25% in 20 min.

후처리

  1. temperaturecooled to 0° C.
  2. customthe orange solid was precipitated
  3. filtrationfiltered
  4. washwashed by water
  5. customRecrystallization from MeOH—H2O

출처 및 근거

ORD 기록
ord-a1edaf39afe243b9bc4864d864bfcb22
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08257931B2

연결된 노트

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