4-Methylmorpholine → 2-(Allyloxy)-N-methoxy-N-methylacetamide

HRID 2060747노트

반응식

HRID 2060747 반응식
S(Cl)(Cl)=O.[CH2:5]([O:8][CH2:9][C:10]([OH:12])=O)[CH:6]=[CH2:7].Cl.[CH3:14][NH:15][O:16][CH3:17].CN1CCOCC1>C1(C)C=CC=CC=1.ClCCl.O>[CH2:5]([O:8][CH2:9][C:10]([N:15]([O:16][CH3:17])[CH3:14])=[O:12])[CH:6]=[CH2:7]

참가 물질

8

반응물 4

HCID 79724-MethylmorpholineHCID 24386Thionyl ChlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 109970062-(Prop-2-en-1-yloxy)acetic acid

생성물 1

HCID 574757612-(Allyloxy)-N-methoxy-N-methylacetamide수율 50%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 6344Dichloromethane용매

반응 조건

온도
65 °C

실험 절차

Thionyl chloride (1.5 L) is added in one portion to a solution of 2-(allyloxy)acetic acid (2.2 Kg, 18.9 mol) in toluene (3.0 L), and the mixture is heated at 65° C. under a nitrogen atmosphere for 1 h. The mixture is cooled to room temperature and is added to a solution of N,O-dimethylhydroxylamine hydrochloride (2.1 Kg, 21.5 mol) and N-methyl morpholine (6.5 L, 59.2 mol) in dichloromethane (19 L) at 5° C. The reaction mixture is stirred at 25° C. for 16 h. Water is added, and the reaction mixture is extracted with dichloromethane. The combined organic phase is collected and washed with 1 M HCl (6 L), dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel chromatography eluting with ethyl acetate in hexanes to afford the title compound (1.49 Kg, 50%). ES/MS m/e: 160 (M+1).

후처리

  1. temperatureThe mixture is cooled to room temperature
  2. extractionthe reaction mixture is extracted with dichloromethane
  3. customThe combined organic phase is collected
  4. washwashed with 1 M HCl (6 L)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-aeea30b8936a48819a70a8f312d1b8dc
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278441B2

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