Chloromethyl Methyl Ether → N-ethyl-N-[2-(methoxymethyl)oxyethyl]aniline

HRID 356227

반응식

HRID 356227 반응식
[CH2:1]([N:3]([CH2:10][CH2:11][OH:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].CCCCCC.[CH3:19][O:20][CH2:21]Cl>O1CCCC1>[CH2:1]([N:3]([CH2:10][CH2:11][O:12][CH2:19][O:20][CH3:21])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 7864Chloromethyl Methyl EtherHCID 8058HexaneHCID 623382-(N-ethylanilino)ethanol

생성물 1

HCID 18941471N-ethyl-N-[2-(methoxymethyl)oxyethyl]aniline수율 89%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

55.7 g (0.34 mol) of N-ethyl-N-(2-hydroxylethyl)aniline was dissolved in 250 ml of anhydrous tetrahydrofuran, and 162 ml (1.2-fold equivalent weight) of a 2.5M hexane solution n-butyllithium was dropwise added thereto over a period of 30 minutes at 0° C. in an atmosphere of argon, followed by stirring at 0° C. for 30 minutes. Next, to the reaction solution obtained, 30.0 g (1.09-fold equivalent weight) of methoxymethyl chloride was dropwise added, and the solution was heated and refluxed for 12 hours, followed by cooling. The precipitate formed was removed by filtration, and thereafter the filtrate obtained was concentrated under reduced pressure. The oily residue thus obtained was distilled under reduced pressure to obtain 63 g of N-ethyl-N-[2-(methoxymethyl)oxyethyl]aniline (yield: 89%).

후처리

  1. customNext, to the reaction solution obtained
  2. temperaturethe solution was heated
  3. temperaturerefluxed for 12 hours
  4. temperatureby cooling
  5. customThe precipitate formed
  6. customwas removed by filtration
  7. customthe filtrate obtained
  8. concentrationwas concentrated under reduced pressure
  9. customThe oily residue thus obtained
  10. distillationwas distilled under reduced pressure

출처 및 근거

ORD 기록
ord-ace98e2e886e4639a8b04a97b855a07a
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834575

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