Ethyl Acetate → 4-Methyl-5-nitro-2-(1,2,4-triazol-1-yl)pyridine

HRID 580847노트

반응식

HRID 580847 반응식
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=1.C(OCC)(=O)C>CN(C=O)C.O>[CH3:19][C:17]1[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=[C:13]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[CH:18]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 3453642-Chloro-4-methyl-5-nitropyridine

생성물 1

HCID 542579534-Methyl-5-nitro-2-(1,2,4-triazol-1-yl)pyridine수율 43%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1,2,4-triazole (4.0 g, 58 mmol) in dry DMF (20 mL) was added potassium carbonate (12.0 g, 87 mmol) and 2-chloro-4-methyl-5-nitropyridine (10 g, 58 mmol) and the mixture stirred at ambient temperature under nitrogen for 24 hours. Ethyl acetate (500 mL) and water (250 mL) were added to the mixture and the resulting precipitate was collected by filtration to give the title compound (5.08 g, 43%) as a pale brown solid. The filtrate was separated and the organic phase was washed with water (250 mL) and brine (250 mL), dried (MgSO4) and evaporated. The residue was triturated with ethyl acetate and the precipitate collected by filtration to give the title compound as a brown solid (4.11 g, 35%, overall yield 78%). mp 198-200° C. 1H NMR (360 MHz, CDCl3) δ 2.72 (3H, s), 7.86 (1H, s), 8.07 (1H, s) 9.03 (1H, s) and 9.15 (1H, s).

후처리

  1. filtrationthe resulting precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-df1f92038f3c46ae88a6180b09be646a
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919783

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