Methanol → 5-[1-(4-bromophenyl)-1-methylethyl]-1H-1,2,4-triazol-3-amine

HRID 900827노트

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HRID 900827 반응식
[N+]([O-])(O)=O.[NH2:5][NH:6][C:7]([NH2:9])=[NH:8].CO.C[O-].[Na+].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:28])([CH3:27])[C:23](OC)=O)=[CH:18][CH:17]=1>O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:28]2[NH:5][N:6]=[C:7]([NH2:9])[N:8]=2)([CH3:27])[CH3:23])=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 3651431Methyl 2-(4-bromophenyl)-2-methylpropanoateHCID 10942334Sodium MethoxideHCID 178513186HCID 178513186, 화합물

생성물 1

HCID 586702735-[1-(4-bromophenyl)-1-methylethyl]-1H-1,2,4-triazol-3-amine수율 31%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

To a stirred mixture of N-aminoguanidine nitrate (2.1 g, 15 mmol) and anhydrous methanol (18 mL) cooled to 0° C. was added sodium methoxide solution (25% in methanol, 3.4 mL, 15 mmol) dropwise. The resulting mixture was stirred at 0° C. for 10 min before methyl 2-(4-bromophenyl)-2-methylpropanoate (1.0 g, 3.9 mmol) was added. The mixture was then stirred at 0° C. for 10 min, RT for 10 min, and 75 ° C. for 6 days. The reaction mixture was cooled and diluted with 20 mL of water. Methanol was removed under vacuum and the aqueous solution was acidified to pH=3-4 with 3 N aqueous HCl solution and extracted with ethyl acetate. The ethyl acetate layer was dried (Na2SO4) and concentrated. Silica gel flash chromatography purification gave 330 mg (31% yield) of the title compound as a yellow solid. (M+H)+=281.14

후처리

  1. additionwas added
  2. wait75 ° C. for 6 days
  3. temperatureThe reaction mixture was cooled
  4. customMethanol was removed under vacuum
  5. extractionextracted with ethyl acetate
  6. dry with materialThe ethyl acetate layer was dried (Na2SO4)
  7. concentrationconcentrated
  8. customSilica gel flash chromatography purification

출처 및 근거

ORD 기록
ord-511b02996a9948c98880de54604fef60
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361654B2

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