2,6-Lutidine → 5-Amino-N-(triethylsilyl)-1H-1,2,4-triazole-3-carboxamide

HRID 1931544ノート

反応式

HRID 1931544 の反応式
[NH2:1][C:2]1[N:6]=[C:5]([C:7]([NH2:9])=[O:8])[NH:4][N:3]=1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:24]([CH2:29][CH3:30])([CH2:27][CH3:28])[CH2:25][CH3:26])(=O)=O>ClCCCl.C(OCC)(=O)C>[NH2:1][C:2]1[N:6]=[C:5]([C:7]([NH:9][Si:24]([CH2:29][CH3:30])([CH2:27][CH3:28])[CH2:25][CH3:26])=[O:8])[NH:4][N:3]=1

参加物

6

反応物 3

HCID 79372,6-LutidineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 187074943-amino-1H-1,2,4-triazole-5-carboxamide(SALTDATA: FREE)

生成物 1

HCID 593125935-Amino-N-(triethylsilyl)-1H-1,2,4-triazole-3-carboxamide収率 26.5%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

A stirred mixture of 3-amino-1H-1,2,4-triazole-5-carboxamide (103 mg, 0.810 mol) in 1,2-dichloroethane (1.62 mL) treated at room temperature with 2,6-lutidine (283 μL, 2.43 mmol) and triethylsilyl trifluoromethanesulfonate (458 μL, 2.03 mmol). After 22 hours the reaction was heated at 50° C. and after 1.5 hours of heating the reaction was allowed to cool to room temperature. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (25 mL), dried over magnesium sulfate, filtered, and evaporated to an oil which was flash chromatographed (silica gel, 0-10% ethyl acetate:hexane) to give the title compound as a white solid (130 mg).

後処理

  1. temperatureof heating the reaction
  2. temperatureto cool to room temperature
  3. washwashed with water (25 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil which
  7. customchromatographed (silica gel, 0-10% ethyl acetate:hexane)

出典と根拠

ORDレコード
ord-5fb4753ee4434cab8649ff79e66580bc
出典データセット
uspto-grants-2012_05
特許番号
US08188085B2

反応ノート

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