Hydrochloric Acid → N,N-dimethyl-m-ethyl-p-phenylenediamine dihydrochloride

HRID 1712011

反応式

HRID 1712011 の反応式
[CH3:1][N:2]([CH3:11])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[CH:4]=1.[ClH:12].[N:13]([O-])=O.[Na+]>O.C(OCC)C.C(O)C.[Fe]>[ClH:12].[ClH:12].[CH3:1][N:2]([CH3:11])[C:3]1[CH:8]=[CH:7][C:6]([NH2:13])=[C:5]([CH2:9][CH3:10])[CH:4]=1

参加物

7

反応物 3

HCID 313Hydrochloric Acid3 回HCID 13756906N,N-dimethyl-m-ethylanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 66863017N,N-dimethyl-m-ethyl-p-phenylenediamine dihydrochloride収率 60%

試薬・触媒・溶媒 3

HCID 23925Iron触媒2 回HCID 962Water溶媒2 回HCID 21585056Diethyl ether ethanol溶媒

反応条件

温度
5 °C

実験手順

To a 250 cm3 round bottom flask was added N,N-dimethyl-m-ethylaniline ((CH3)2NC6H4CH2CH3, MW 149.23, 4.68 g, 31.3 mmol), water (100 cm3), and hydrochloric acid (HCl, 8.5 cm3, 37%). The solution was cooled to 5° C. A solution of sodium nitrite (NaNO2, MW 69.0, 2.46 g, 35.7 mmol) in water (80 cm3) was then added dropwise. The mixture was stirred for 3 hours at room temperature. Iron fillings (Fe, MW 55.85, 5.24 g, 94 mmol) and hydrochloric acid (HCl, 8.5 cm3, 37%) were added. The mixture was stirred at room temperature for 3 hours. The mixture was filtered, and the filtrate collected. The pH of the filtrate was adjusted to pH 7 using sodium bicarbonate (NaHCO3) solution, and extracted into ethyl acetate (3×50 cm3). The combined extracts were dried over magnesium sulfate (MgSO4). The mixture was filtered and the filtrate concentrated to yield a brown oil. The oil was dissolved in diethyl ether/ethanol (1:1) (175 cm3). Hydrochloric acid (HCl, 5 cm3, 37%) was added. The solution was filtered to give the product, N,N-dimethyl-m-ethyl-p-phenylenediamine dihydrochloride ((CH3)2NC6H4(CH2CH3)NH2.2HCl, MW 237.17, 4.44 g, 1.87 mmol, 60%) as a light brown solid. δH (250 MHz; D2O): 7.66 (1H, s, ArH), 7.56 (2H, s, ArH), 3.29 (6H, s, NCH3), 2.74 (2H, q, 7.5, CH2), 1.25 (3H, t, 7.5, CH3); δC (62.9 MHz; CDCl3): 15.5 (CH3) 25.6 (NCH2), 48.9 (NCH3), 122.1 (ArC), 124.6 (ArC), 128.1 (ArC), 132.6 (ArC), 143.3 (ArC), 144.9 (ArC).

後処理

  1. additionwere added
  2. stirringThe mixture was stirred at room temperature for 3 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate collected
  5. extractionextracted into ethyl acetate (3×50 cm3)
  6. dry with materialThe combined extracts were dried over magnesium sulfate (MgSO4)
  7. filtrationThe mixture was filtered
  8. concentrationthe filtrate concentrated
  9. customto yield a brown oil
  10. filtrationThe solution was filtered

出典と根拠

ORDレコード
ord-06c8ec8fe9a5493385c5bf5c6af22b99
出典データセット
uspto-grants-2010_09
特許番号
US07790881B2

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