Methylamine → 2,6-Dimethyl-4-[3-(methylamino)-4-nitrophenoxy]aniline

HRID 424866노트

반응식

HRID 424866 반응식
Cl[C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][NH2:13].[NH2:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([OH:22])=[CH:17][C:16]=1[CH3:23].CC(C)([O-])C.[K+]>CN(C)C(=O)C.O>[NH2:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([O:22][C:6]2[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:13][CH3:12])[CH:7]=2)=[CH:17][C:16]=1[CH3:23]

참가 물질

7

반응물 4

HCID 6329MethylamineHCID 118992,4-DichloronitrobenzeneHCID 765434-Amino-3,5-dimethylphenolHCID 23665647Potassium tert-butoxide

생성물 1

HCID 667016652,6-Dimethyl-4-[3-(methylamino)-4-nitrophenoxy]aniline수율 67%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매2회

반응 조건

온도
77.5 °C

실험 절차

To a solution of 2,4-dichloronitrobenzene (3.0 g) in N,N-dimethylacetamide (30 ml) was added a 40% aqueous solution of methylamine (4.9 g) at room temperature, and the resulting mixture was stirred at 75-80° C. for 1.5 hours. To the reaction mixture were added 4-amino-3,5-dimethylphenol (2.2 g), potassium t-butoxide (3.5 g), and N,N-dimethylacetamide (15 ml), and the resulting mixture was stirred at the same temperature for 3 hours. After stirring, water (60 ml) was added to the reaction mixture, and the resulting mixture was cooled gradually to room temperature. The crystalline solid precipitated was collected by filtration and dried in vacuo to afford the title compound (3.0 g, yield: 67%) as a yellow crystalline solid.

후처리

  1. stirringthe resulting mixture was stirred at the same temperature for 3 hours
  2. stirringAfter stirring
  3. temperaturethe resulting mixture was cooled gradually to room temperature
  4. customThe crystalline solid precipitated
  5. filtrationwas collected by filtration
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-60ec85ea250846e98d6e30b990b75e47
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106079B2

반응 노트

불러오는 중…