Aniline → N,N-dihexadecylaniline

HRID 329353노트

반응식

HRID 329353 반응식
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C([N:28]([CH:31]([CH3:33])[CH3:32])[CH2:29][CH3:30])(C)C>C1(C)C=CC=CC=1>[CH2:9]([N:28]([CH2:29][CH2:30][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:2])[C:31]1[CH:32]=[CH:11][CH:10]=[CH:9][CH:33]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

참가 물질

5

반응물 3

HCID 6115AnilineHCID 110071-IodohexadecaneHCID 81531Diisopropylethylamine

생성물 1

HCID 5102033N,N-dihexadecylaniline수율 48%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

Aniline (0.93 g), 1-iodohexadecane (10.56 g) and diisopropylethylamine (2.58 g) were combined in 10 ml of toluene. The mixture was heated at about 100° C. for a period of three days. The mixture was chromatographed on a silica gel column using 1% ethyl acetate in hexane. The heavy crystalline mass that precipitated from solution was cooled, diluted with ether and filtered. The filtrate was concentrated to an oil and applied to a silica gel column. The oil was washed with 500 ml of hexane followed by 1% ethyl acetate in hexane. The dialkylated fractions were combined and evaporated to give 2.6 grams of product.

후처리

  1. customThe mixture was chromatographed on a silica gel column
  2. customThe heavy crystalline mass that precipitated from solution
  3. temperaturewas cooled
  4. additiondiluted with ether
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated to an oil
  7. washThe oil was washed with 500 ml of hexane
  8. customevaporated

출처 및 근거

ORD 기록
ord-e85b1ee711064a0684646b2befec4d4a
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04891324

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