1,1-Dimethylhydrazine → 7-chloro-N',N'-dimethylthieno[3,2-b]pyridine-2-carbohydrazide

HRID 418672ノート

反応式

HRID 418672 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11](Cl)=[O:12])[S:10][C:3]=12.[CH3:14][N:15]([CH3:17])[NH2:16]>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([NH:16][N:15]([CH3:17])[CH3:14])=[O:12])[S:10][C:3]=12

参加物

5

反応物 2

HCID 59761,1-Dimethylhydrazine2 回HCID 221435437-Chlorothieno[3,2-b]pyridine-2-carbonyl chloride

生成物 1

HCID 587901507-chloro-N',N'-dimethylthieno[3,2-b]pyridine-2-carbohydrazide収率 72.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of 7-chlorothieno[3,2-b]pyridine-2-carbonyl chloride 20 (1 g, 4.33 mmol) (scheme 6) in DCM (22 mL), 1,1-dimethylhydrazine (0.33 mL, 4.33 mmol) was added in one portion and the mixture was stirred for 5 h. More 1,1-dimethylhydrazine (0.33 mL, 4.33 mmol) was added and the mixture was stirred overnight at room temperature. The crude was diluted with EtOAc, extracted with 1N HCl, the aqueous solution basified to pH˜11 by addition of 1N NaOH, extracted with EtOAc, the organic phase dried over anhydrous Na2SO4 and concentrated under reduced pressure affording 237 (798 mg, 3.13 mmol, 72%) as a crude mixture that was used in the next step without further purification. MS (m/z): (M+1) 255.9 (100%), 257.9 (39%).

後処理

  1. additionwas added in one portion
  2. stirringthe mixture was stirred overnight at room temperature
  3. extractionextracted with 1N HCl
  4. additionthe aqueous solution basified to pH˜11 by addition of 1N NaOH
  5. extractionextracted with EtOAc
  6. dry with materialthe organic phase dried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-688e8c6d13144707b20963aff80b258a
出典データセット
uspto-grants-2012_01
特許番号
US08093264B2

反応ノート

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