Hydrazine hydrate (1:1) → HCID 69419623, 화합물

HRID 1766982노트

반응식

HRID 1766982 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:10]=1[CH:11]=O)=[O:5])[CH3:2].O.[NH2:28][NH2:29]>C(O)(=O)C.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:9]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[C:10]=1[CH:11]=[N:28][NH2:29])=[O:5])[CH3:2]

참가 물질

5

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 58760951HCID 58760951, 화합물

생성물 1

HCID 69419623HCID 69419623, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 1140Toluene용매

실험 절차

A solution of 1-(4-chloro-phenyl)-2-(2-chloro-phenyl)-5-formyl-1H-imidazole-4-carboxylic acid ethyl ester (I-2e, 102 mg, 0.26 mmol), aqueous hydrazine hydrate (50% solution, 0.6 mmol) and glacial acetic acid (1 drop) was heated under reflux in toluene (3 ml) for 18 hours. After cooling to room temperature, the reaction mixture was concentrated in vacuo. The residue was partitioned between CH2Cl2 and sat'd aq. NaHCO3. The organic solution was dried and concentrated in vacuo. Purification using 2 mm chromatotron plates and a solvent gradient of 1:1 EtOAc/hexanes to 100% EtOAc provided the desired product I-2f (Rf=0.8, 100% EtOAc, 62 mg): +APCI MS (M+1) 403.1; 1H NMR (CD2Cl2) δ 1.40 (3H, t), 4.37 (2H, q), 5.60 (2H, br s), 7.10–7.14 (2H, m), 7.21–7.25 (3H, m), 7.29–7.33 (3H, m), 8.40 (1H, s).

후처리

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between CH2Cl2
  3. customThe organic solution was dried
  4. concentrationconcentrated in vacuo
  5. customPurification

출처 및 근거

ORD 기록
ord-b9f9201d8b744e54b3c40598b842075e
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07232823B2

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