Dimethylformamide → methyl 1-(4-nitrobenzyl)-1H-1,2,4-triazole-5-carboxylate

HRID 30685

반응식

HRID 30685 반응식
[NH:1]1[CH:5]=[N:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]1.[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1)([O-:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:2]2[C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:4][CH:5]=[N:1]2)=[CH:15][CH:14]=1)([O-:12])=[O:11]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 178499122HCID 178499122, 화합물

생성물 1

HCID 69209378methyl 1-(4-nitrobenzyl)-1H-1,2,4-triazole-5-carboxylate수율 12.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of methyl 1H-1,2,4-triazole-3-carboxylate (7.06 g), 4-nitrobenzyl bromide (10 g), potassium carbonate (16.6 g) and N,N-dimethylformamide (60 ml) was stirred at room temperature for 4 hrs. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give methyl 1-(4-nitrobenzyl)-1H-1,2,4-triazole-5-carboxylate (1.50 g, 12%) as crystals from a fraction eluted with hexane-ethyl acetate (1:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 126-130° C.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-45fd186c4b9f4f51b637c81be0fea8c5
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423159B2

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