Hydrazine hydrate (1:1) → HCID 69419623、化合物

HRID 1766982ノート

反応式

HRID 1766982 の反応式
[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]

参加物

5

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 58760951HCID 58760951、化合物

生成物 1

HCID 69419623HCID 69419623、化合物

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b9f9201d8b744e54b3c40598b842075e
出典データセット
uspto-grants-2007_06
特許番号
US07232823B2

反応ノート

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