Toluene → N,2,5-trimethyl-N-phenylaniline

HRID 227845

반응식

HRID 227845 반응식
CC([O-])(C)C.[Na+].C1(C)C=CC=CC=1.[CH3:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=1[CH3:30]>CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:30][C:24]1[CH:25]=[CH:26][C:27]([CH3:29])=[CH:28][C:23]=1[N:15]([CH3:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 7515N-MethylanilineHCID 32883Chloro-p-xyleneHCID 23676156Sodium t-butoxide

생성물 1

HCID 11042050N,2,5-trimethyl-N-phenylaniline수율 95%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 3283Diethyl Ether용매

반응 조건

온도
80 °C

실험 절차

An oven-dried test tube was purged with argon and charged with Pd2(dba)3 (4.6 mg, 0.005 mmol, 1.0 mol % Pd), 2 [Example 1] (6.0 mg, 0.015 mmol, 1.5 mol %), and NaOt-Bu (135 mg, 1.40 mmol). The test tube was fitted with a septum, then toluene (2.0 mL), N-methylaniline (135 μL, 1.25 mmol), and 2-chloro-p-xylene (135 μL, 1.01 mmol) were added. The mixture was stirred at 80° C. for 13 h, then cooled to room temperature, diluted with ether (20 mL), filtered and concentrated. The crude material was purified by flash chromatography on silica gel to afford 202 mg (95%) of a colorless oil.

후처리

  1. customAn oven-dried test tube was purged with argon
  2. customThe test tube was fitted with a septum
  3. temperaturecooled to room temperature
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-903dbd7f86834deb842b14999b59d176
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560582B2

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