Sodium hydride → N,N-Dimethyl-2-(3-methyl-4-nitro-pyrazol-1-yl)-acetamide

HRID 445542ノート

反応式

HRID 445542 の反応式
[CH3:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][NH:4][N:3]=1.[H-].[Na+].Br[CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15]>CN(C=O)C>[CH3:17][N:16]([CH3:18])[C:14](=[O:15])[CH2:13][N:4]1[CH:5]=[C:6]([N+:7]([O-:9])=[O:8])[C:2]([CH3:1])=[N:3]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 2255442-Bromo-N,N-dimethylacetamideHCID 178434564HCID 178434564、化合物

生成物 1

HCID 59619688N,N-Dimethyl-2-(3-methyl-4-nitro-pyrazol-1-yl)-acetamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 3-methyl-4-nitropyrazole (Apollo, Cheshire, UK, 500 mg, 3.93 mmol) in DMF (10 ml) was added 55% NaH in oil (198 mg, 4.54 mmol) and the reaction mixture was stirred for 30 min at rt. Then to the reaction mixture was added a solution of 2-bromo-N,N-dimethylacetamide (stage L.3, 720 mg, 4.34 mmol) in DMF (3 ml). The reaction mixture was stirred for 1 h at it then quenched with saturated aqueous NaHCO3 and extracted with EtOAc (2×). The combined organic layers were washed with water (2×), brine, dried over Na2SO4, filtered and evaporated. The crude product was purified by Prep. HPLC (H2O (0.1% TFA)/CH3CN 97:2 to 75:25; reverse phase silica gel). The fractions containing product were collected together, basified with NaHCO3 and concentrated before being extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to give the title compound as a white solid (HPLC tR 2.06 min (Method A); M+H=213 MS-ES).

後処理

  1. stirringThe reaction mixture was stirred for 1 h at it
  2. customthen quenched with saturated aqueous NaHCO3
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic layers were washed with water (2×), brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by Prep
  9. additionThe fractions containing product
  10. customwere collected together
  11. concentrationconcentrated
  12. extractionbefore being extracted with EtOAc (3×)
  13. washThe combined organic layers were washed with brine
  14. dry with materialdried over Na2SO4
  15. filtrationfiltered
  16. customevaporated

出典と根拠

ORDレコード
ord-d1dca7afad944ad1b46e68a8403c68b5
出典データセット
uspto-grants-2013_07
特許番号
US08476294B2

反応ノート

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