Cesium carbonate → N-(3-(1H-tetrazol-1-yl)propyl)-2-fluoro-4-nitroaniline

HRID 56191ノート

反応式

HRID 56191 の反応式
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH:9]=[N:8][N:7]=[N:6]1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:16][C:17]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:18]=1[NH2:19]>CN(C=O)C>[N:5]1([CH2:4][CH2:3][CH2:2][NH:19][C:18]2[CH:20]=[CH:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:17]=2[F:16])[CH:9]=[N:8][N:7]=[N:6]1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 1012542-Fluoro-4-nitroanilineHCID 230546531-(3-Chloropropyl)-1H-tetrazole

生成物 1

HCID 90031425N-(3-(1H-tetrazol-1-yl)propyl)-2-fluoro-4-nitroaniline収率 14.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 1-(3-chloropropyl)-1H-tetrazole (2.10 g, 14.33 mmol), cesium carbonate (4.66 g, 14.33 mmol) and a catalytic amount of KI in DMF (30 mL) in an ice bath was added 2-fluoro-4-nitroaniline (1.50 g, 9.61 mmol) in one portion. After the mixture was refluxed for 35 h, the mixture was cooled to rt and filtered. The filtrate was concentrated in vacuo. To the residue was added water (50 mL) and the resulting mixture was extracted with DCM (20 mL 2). The combined organic layers were washed with brine (20 mL×2) and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as oil (0.36 g, 10%).

後処理

  1. temperatureAfter the mixture was refluxed for 35 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. additionTo the residue was added water (50 mL)
  5. extractionthe resulting mixture was extracted with DCM (20 mL 2)
  6. washThe combined organic layers were washed with brine (20 mL×2)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

出典と根拠

ORDレコード
ord-772ee64676df4d7c813976919083bbc8
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

反応ノート

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