Triethylamine → 1-(4-methoxyphenyl)-N-(1,1,1-trifluoropropan-2-ylidene)methanamine

HRID 2202530노트

반응식

HRID 2202530 반응식
[F:1][C:2]([F:7])([F:6])[C:3](=O)[CH3:4].[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1.C(N(CC)CC)C>C(OCC)C.CCCCCC.Cl[Ti](Cl)(Cl)Cl>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:15]=[C:3]([CH3:4])[C:2]([F:7])([F:6])[F:1])=[CH:12][CH:11]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 9871Methyl trifluoromethyl ketoneHCID 754524-Methoxybenzylamine

생성물 1

HCID 866576701-(4-methoxyphenyl)-N-(1,1,1-trifluoropropan-2-ylidene)methanamine

시약·촉매·용매 3

HCID 24193Titanium Tetrachloride촉매HCID 3283Diethyl Ether용매2회HCID 8058Hexane용매

실험 절차

To a stirring solution of trifluoroacetone (7.75 g, 69.2 mmol) in diethyl ether (60 ml) at −40° C. was added 4-methoxybenzyl amine (9.49 g, 69.2 mmol) and triethylamine (14 g, 138 mmol) in diethyl ether (40 ml). A cooled (0° C.) mixture of TiCl4 (6.56 g, 34.6 mmol) in hexane (40 ml) at was added dropwise over 10 minutes and the resulting mixture was allowed to warm up to ambient temperature over 20 mins and stirred at 50° C. for 2.5 h. The inorganic precipitate was removed by filtration and washed with diethyl ether. The filtrate was concentrated in vacuo to afford a yellow oil. Purification of the crude product by chromatography on silica eluting with 0% to 25% EtOAc in iso-hexane afforded the title product.

후처리

  1. temperatureA cooled
  2. additionat was added dropwise over 10 minutes
  3. customThe inorganic precipitate was removed by filtration
  4. washwashed with diethyl ether
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto afford a yellow oil
  7. customPurification of the crude product by chromatography on silica eluting with 0% to 25% EtOAc in iso-hexane

출처 및 근거

ORD 기록
ord-1e4e6968013f4e279cbb026ff093b902
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365552B2

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