Sodium hydride → 2-(3-nitro-1H-pyrazol-1-yl)acetamide

HRID 546010노트

반응식

HRID 546010 반응식
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:12][C:13]([NH2:15])=[O:14]>CN(C)C=O>[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:12][C:13]([NH2:15])=[O:14])[N:5]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 178526745HCID 178526745, 화합물

생성물 1

HCID 401765862-(3-nitro-1H-pyrazol-1-yl)acetamide수율 48%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-nitro-1H-pyrazole (prepared in example 3, 150 mg, 1.33 mmol) in anhydrous N,N-dimethylformamide (2 mL), a 60% dispersion of sodium hydride in mineral oil (58 mg, 1.46 mmol) was added while stirring under nitrogen. After the effervescence ceased and the mixture was stirred for additional 30 min, bromoacetamide (201 mg, 1.46 mmol) was added. The mixture was continued to stir under nitrogen for an additional 2 h. The solvent was removed in vacuo and purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded 2-(3-nitro-pyrazol-1-yl)-acetamide (107 mg, 48%) as a white solid.

후처리

  1. stirringthe mixture was stirred for additional 30 min
  2. stirringto stir under nitrogen for an additional 2 h
  3. customThe solvent was removed in vacuo and purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% ethyl acetate/hexanes to 50% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-d95c2cabeeea49a28f0df0d50967addb
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935699B2

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