Triethylamine → Methyl 3-{[[2-(diethylamino)ethyl](methyl)amino]methyl}-5-methylbenzoate

HRID 348920

반응식

HRID 348920 반응식
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].C(N(CC)CC)C.CS(Cl)(=O)=O.[CH2:26]([N:28]([CH2:33][CH3:34])[CH2:29][CH2:30][NH:31][CH3:32])[CH3:27]>C(Cl)Cl>[CH2:26]([N:28]([CH2:33][CH3:34])[CH2:29][CH2:30][N:31]([CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])[CH3:32])[CH3:27]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 660341,2-Ethanediamine, N1,N1-diethyl-N2-methyl-HCID 21086184Methyl 3-(hydroxymethyl)-5-methylbenzoate

생성물 1

HCID 21086144Methyl 3-{[[2-(diethylamino)ethyl](methyl)amino]methyl}-5-methylbenzoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To an ice-cold, stirred solution of methyl 3-(hydroxymethyl)-5-methylbenzoate (200 mg, 1.19 mmol) and triethylamine (241 mg, 2.38 mmol) in methylene chloride (5 mL) is added methanesulfonyl chloride (191 mg, 1.67 mmol). The reaction mixture is stirred for 15 min, the precipitate that formed is removed by filtration, and N,N-diethyl-N′-methylethylenediamine (465 mg, 3.57 mmol) was added. The reaction mixture is stirred at room temperature for 2 h and then concentrated under reduced pressure. Purification by flash column chromatography (silica, 9:1 chloroform/methanol) gives the title compound. 1H NMR (300 MHz, CDCl3) δ 8.02 (s, 2H), 7.33 (s, 1H), 3.56 (s, 3H), 3.48 (s, 2H), 2.95 (m, 4H), 2.75 (m, 4H), 2.41 (s, 3H), 2.31 (s, 3H), 1.21 (m, 6H).

후처리

  1. customthe precipitate that formed
  2. additionwas added
  3. stirringThe reaction mixture is stirred at room temperature for 2 h
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (silica, 9:1 chloroform/methanol)

출처 및 근거

ORD 기록
ord-d22768786d2541f198156eeb45ac8706
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

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