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

HRID 56191노트

반응식

HRID 56191 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-772ee64676df4d7c813976919083bbc8
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434695B2

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