Diethyl Ether → [1-ethyl-5-(4-methoxy-phenyl)-1H-1,2,4-triazol-3-yl]-carbamic acid benzyl ester

HRID 386894ノート

反応式

HRID 386894 の反応式
C(N(CC)C(C)C)(C)C.[CH2:10]([O:17][C:18]([NH:20][C:21](=[N:24][C:25](=O)[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)SC)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)(=O)C(O)=O.[CH2:41]([NH:43][NH2:44])[CH3:42].CCOCC>CN(C=O)C>[CH2:10]([O:17][C:18](=[O:19])[NH:20][C:21]1[N:24]=[C:25]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[N:43]([CH2:41][CH3:42])[N:44]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 178491619HCID 178491619、化合物

生成物 1

HCID 59253256[1-ethyl-5-(4-methoxy-phenyl)-1H-1,2,4-triazol-3-yl]-carbamic acid benzyl ester収率 92.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

N,N-diisoproylethylamine (9.9 g, 76.8 mmol) is added to a solution of 1-benzyloxycarbonyl-3-(4-methoxy-benzoyl)-2-methyl-isothiourea (11.0 g, 30.7 mmol) and ethyl hydrazine oxalate (11.6 g, 76.8 mmol) in DMF (110.0 mL) and the reaction mixture is heated at 50° C. for 12 h. Ice and ether are added to the reaction mixture and the two phases are separated. The organic phase is dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford 10 g of [1-ethyl-5-(4-methoxy-phenyl)-1H-1,2,4-triazol-3-yl]-carbamic acid benzyl ester that is used in the next step without further purification. m/z 353 [M+H].

後処理

  1. customthe two phases are separated
  2. dry with materialThe organic phase is dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-0b68cf93164c4ec4b74a1debac3b5bb1
出典データセット
uspto-grants-2013_02
特許番号
US08372874B2

反応ノート

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