N-Methylbenzylamine → 5-acetonyl-3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazole

HRID 247112노트

반응식

HRID 247112 반응식
[CH2:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10]Cl)[N:6]=1)[C:2]([CH3:4])=[O:3].[CH3:12][NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.C(Cl)(Cl)Cl.CO>CN(C=O)C>[CH2:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10][N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:12])[N:6]=1)[C:2]([CH3:4])=[O:3]

참가 물질

6

반응물 4

HCID 7669N-MethylbenzylamineHCID 8471TriethylamineHCID 138247055-Acetonyl-3-chloromethyl-1,2,4-oxadiazoleHCID 21584188Chloroform methanol

생성물 1

HCID 201612565-acetonyl-3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazole수율 65.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 800 mg of 5-acetonyl-3-chloromethyl-1,2,4-oxadiazole, 720 mg of N-methylbenzylamine and 1.0 g of triethylamine in 5 ml of DMF was stirred at room temperature for 8 hours. The reaction mixture was then poured into ice-water and the resultant mixture was extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo to yield a brown oil. Chromatography on silica gel using chloroform-methanol (20:1, v/v) as eluent afforded 780 mg of 5-acetonyl-3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazole as a colorless oil, IR νmaxneat cm-1 : 1730, 1635, 1580, 1545, 1450, 1360.

후처리

  1. extractionthe resultant mixture was extracted with ethyl acetate
  2. washThe extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto yield a brown oil

출처 및 근거

ORD 기록
ord-303c850ae3a546e8b488f5e8da837353
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04705786

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