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

HRID 900827ノート

反応式

HRID 900827 の反応式
[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

参加物

6

反応物 4

HCID 887MethanolHCID 3651431Methyl 2-(4-bromophenyl)-2-methylpropanoateHCID 10942334Sodium MethoxideHCID 178513186HCID 178513186、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-511b02996a9948c98880de54604fef60
出典データセット
uspto-grants-2008_04
特許番号
US07361654B2

反応ノート

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