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

HRID 386894Notes

Reaction equation

HRID 386894 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

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].

Workup

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

Sources & evidence

ORD record
ord-0b68cf93164c4ec4b74a1debac3b5bb1
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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