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

HRID 386894노트

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HRID 386894 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

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].

후처리

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

출처 및 근거

ORD 기록
ord-0b68cf93164c4ec4b74a1debac3b5bb1
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372874B2

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