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

HRID 2382615

반응식

HRID 2382615 반응식
[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+].NC1C=CC=CC=1>C(O)C.[Fe].C(OCC)C.O>[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

참가 물질

9

반응물 4

HCID 313Hydrochloric Acid3회HCID 6115AnilineHCID 13756906N,N-dimethyl-m-ethylanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 66863017N,N-dimethyl-m-ethyl-p-phenylenediamine dihydrochloride수율 72%

시약·촉매·용매 4

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매HCID 3283Diethyl Ether용매

반응 조건

온도
5 °C

실험 절차

To a 250 cm3 round bottom flask was added N,N-dimethyl-m-ethylaniline (4.68 g, 31.3 mmol), water (100 cm3) and hydrochloric acid (8.5 cm3, 37%) and the solution was cooled to 5° C. An aqueous (80 cm3) solution of sodium nitrite (2.46 g, 3.57 mmol) was then added dropwise to the aniline mixture and stirred for 3 hours at room temperature. Iron (Fe) fillings (5.24 g, 94 mmol) and hydrochloric acid (8.5 cm3, 37%) were added and the mixture was stirred at room temperature for 3 hours. The suspension was filtered and the filtrate adjusted to pH 7 with sodium bicarbonate solution before extraction into ethyl acetate (3×50 cm3). The combined extracts were dried over magnesium sulphate, filtered, and concentrated to yield a brown oil. The oil was dissolved in ethanol (100 cm3) and diethyl ether (80 cm3) and hydrochloric acid (7 cm3, 37%) was added carefully to give the title compound (7.42 g, 72%) as a light tan solid. νmax (KBr)/cm−1: 2976 (CH), 2894 (CH), 2859 (CH), 2753 (CH), 1583 (C═N), 1508 (CH), 1486 (CH), 1459 (CH), 1183 (CM); 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).

후처리

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. filtrationThe suspension was filtered
  3. extractionthe filtrate adjusted to pH 7 with sodium bicarbonate solution before extraction into ethyl acetate (3×50 cm3)
  4. dry with materialThe combined extracts were dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a brown oil

출처 및 근거

ORD 기록
ord-02b8edb472314f689ae462b557ba9545
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263589B2

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