N,N-Dimethylethylenediamine → HCID 10244493、化合物

HRID 1160628ノート

反応式

HRID 1160628 の反応式
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].Cl[C:8]1[N:9]=[N+:10]([O-:20])[C:11]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:12]=2[N:13]=1>COCCOC>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:11]2[N+:10]([O-:20])=[N:9][C:8]([NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[N:13][C:12]=2[CH:14]=1

参加物

4

反応物 2

HCID 66053N,N-DimethylethylenediamineHCID 16081296HCID 16081296、化合物

生成物 1

HCID 10244493HCID 10244493、化合物収率 68%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

N,N-Dimethyl-1,2-ethanediamine (1.33 mL, 12.1 mmol) was added to a stirred solution of chloride 7 (0.85 g, 4.04 mmol) in DME (50 mL) and the solution stirred at reflux temperature for 16 h. The solvent was evaporated and the residue was partitioned between DCM (100 mL) and dilute aqueous NH3 (50 mL). The organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-5%) of MeOH/DCM, to give amine 8 (0.72 g, 68%) which was dissolved in HCl-saturated MeOH, the solvent evaporated and the residue crystallized as a tan solid, mp (MeOH/EtOAc) 236-239° C.; 1H NMR [(CD3)2SO] δ 10.68 (br s, 1 H, NH+Cl−), 8.07 (d, J=9.3 Hz, 1 H, H-8), 8.03 (br s, 1 H, NH), 6.95-6.99 (m, 2 H, H-5, H-7), 3.92 (s, 3 H, OCH3), 3.70-3.76 (m, 2 H, CH2N), 3.30-3.35 (m, 2 H, CH2N), 2.81 [d, J=4.9 Hz, 6 H, N(CH3)2]; 13C NMR [(CD3)2SO] δ 164.9, 159.0, 150.4, 125.4, 121.6, 117.3, 104.3, 55.2, 55.0, 42.3 (2), 35.8. Anal. Calcd for C12H18ClN5O2: C, 48.1; H, 6.1; N, 23.4; Cl, 11.8. Found: C, 48.3; H, 6.1; N, 23.6; Cl, 11.9%.

後処理

  1. temperatureat reflux temperature for 16 h
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between DCM (100 mL) and dilute aqueous NH3 (50 mL)
  4. customThe organic fraction was dried
  5. customthe solvent evaporated
  6. customThe residue was purified by chromatography
  7. washeluting with a gradient (0-5%) of MeOH/DCM

出典と根拠

ORDレコード
ord-e56f2bcb6d234b83b5bbfa2e0d8d4c5e
出典データセット
uspto-grants-2010_10
特許番号
US07816521B2

反応ノート

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