Bicarbonate Ion → HCID 67283381、化合物

HRID 1253817ノート

反応式

HRID 1253817 の反応式
[CH3:1][NH:2][C:3]1[C:4]([NH2:12])=[CH:5][CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1.[F:13][C:14]([F:19])([F:18])[C:15](O)=O.C(=O)(O)[O-]>Cl.C(Cl)Cl>[CH3:1][N:2]1[C:3]2[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=2[N:12]=[C:15]1[C:14]([F:19])([F:18])[F:13]

参加物

6

反応物 3

HCID 769Bicarbonate IonHCID 6422Trifluoroacetic acidHCID 21956374N~2~-Methyl-4-nitrobenzene-1,2-diamine

生成物 1

HCID 67283381HCID 67283381、化合物収率 20.4%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid触媒HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

A 250 ml round bottomed flask was charged with N1-methyl-5-nitrobenzene-1,2-diamine (29 g, 0.16 mol), trifluoroacetic acid (22 ml, 0.24 mol) and a few drops of concentrated HCl. A minimum amount of DCM (˜20 ml) was added so that the solid mixture was stirring. The reaction mixture was heated to 70° C. for 12 hours forming a dark brown liquid. The reaction mixture was allowed to cool to room temperature, basified by the slow addition of saturated bicarbonate solution, and extracted into ethyl acetate. The aqueous layer was further extracted twice with ethyl acetate. The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. The compound was purified by flash column chromatography (10 to 20% ethyl acetate/petrol) to afford the title compound (8 g, 20% yield). 1H NMR (DMSO D6, 400 MHz) 4.2 (3H, s), 8.05 (1H, d), 8.35 (1H, d), 8.55 (1H, s); MS (ES+) 246.

後処理

  1. customforming a dark brown liquid
  2. temperatureto cool to room temperature
  3. extractionextracted into ethyl acetate
  4. extractionThe aqueous layer was further extracted twice with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe compound was purified by flash column chromatography (10 to 20% ethyl acetate/petrol)

出典と根拠

ORDレコード
ord-03878b387a8341e5b0be38436a5f0fdf
出典データセット
uspto-grants-2013_06
特許番号
US08455507B2

反応ノート

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