Potassium Carbonate → 1-(2-Chloro-5-methyl-3-pyridylmethyl)2-nitroiminoimidazolidine

HRID 413472

反応式

HRID 413472 の反応式
[Cl:1][C:2]1[C:7]([CH2:8]Cl)=[CH:6][C:5]([CH3:10])=[CH:4][N:3]=1.[N+:11]([N:14]=[C:15]1[NH:19][CH2:18][CH2:17][NH:16]1)([O-:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Cs+]>C(#N)C>[Cl:1][C:2]1[C:7]([CH2:8][N:16]2[CH2:17][CH2:18][NH:19][C:15]2=[N:14][N+:11]([O-:13])=[O:12])=[CH:6][C:5]([CH3:10])=[CH:4][N:3]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 24293Cesium ChlorideHCID 112060822-Chloro-3-(chloromethyl)-5-methylpyridineHCID 135413413N-nitroimidazolidin-2-imine

生成物 1

HCID 1363477121-(2-Chloro-5-methyl-3-pyridylmethyl)2-nitroiminoimidazolidine収率 90%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

2-chloro-3-chloromethyl-5-methylpyridine (1.3 g, 0.0076 moles) was added to a well-stirred material comprising of 2-nitroimino-1, 3-diazacyclopentane (1.18 g, 0.00912 moles), potassium carbonate (1.16 g, 0.0083 moles), cesium chloride (0.04 g, 0.00024 moles) in acetonitrile (10 ml) solvent at room temperature. The reaction mixture was refluxed for 5 hours. Solvent was removed under reduced pressure and the mass diluted with water (25 ml). The mass was then extracted with methylene chloride (2×50 ml) and the layers were separated. Organic layer was dried over sodium sulphate and solvent removed under reduced pressure. The residue obtained was subjected to chromatographic purification on silica gel to give 1-(2-chloro-5-methyl-3-pyridylmethyl)-2-nitroiminoimidazolidine in 90% yield. NMR (CDCl3+DMSO d6): δ2.38 (s, 3H, CH3), 3.58 (t, 2H, N—CH2), 3.74 (t, 2H, N—CH2), 4.52 (s, 2H, CH2), 7.54 (s, 1H, aromatic), 812 (s, 1H, aromatic), 8.86 (1H, NH). Mass: M+. 269.

後処理

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. customSolvent was removed under reduced pressure
  3. additionthe mass diluted with water (25 ml)
  4. extractionThe mass was then extracted with methylene chloride (2×50 ml)
  5. customthe layers were separated
  6. dry with materialOrganic layer was dried over sodium sulphate and solvent
  7. customremoved under reduced pressure
  8. customThe residue obtained
  9. customwas subjected to chromatographic purification on silica gel

出典と根拠

ORDレコード
ord-7586f01012af4ed18c167210e9a16ebd
出典データセット
uspto-grants-2003_05
特許番号
US06566528B1

関連ノート

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