Hydrazinecarboxylic acid, ethyl ester → 6-Ethyl-5-(2-phenyl-benzoxazol-6-yl)-3,6-dihydro-[1.3.4]oxadiazin-2-one

HRID 1619961Notes

Reaction equation

HRID 1619961 reaction equation
[OH:1][CH:2]([CH2:20][CH3:21])[C:3]([C:5]1[CH:19]=[CH:18][C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:11][C:7]=2[CH:6]=1)=O.[NH:22]([C:24](OCC)=[O:25])[NH2:23].[Na]>Cl.C(O)C>[CH2:20]([CH:2]1[O:1][C:24](=[O:25])[NH:22][N:23]=[C:3]1[C:5]1[CH:19]=[CH:18][C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:11][C:7]=2[CH:6]=1)[CH3:21]

Participants

6

Reactant 3

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 5360545SodiumHCID 674627762-Hydroxy-1-(2-phenyl-benzoxazol-6-yl)-butan-1-one

Product 1

HCID 674645236-Ethyl-5-(2-phenyl-benzoxazol-6-yl)-3,6-dihydro-[1.3.4]oxadiazin-2-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent3×

Procedure

50 mg (178 μmol) 2-hydroxy-1-(2-phenyl-benzoxazol-6-yl)-butan-1-one are refluxed together with 20.36 mg (196 μmol) ethyl hydrazinoformate, 1 drop of 0.1N hydrochloric acid and 500 μl ethanol for 10 min, then the solvent is completely removed i. V. The residue is dissolved in 2 ml dry ethanol. 40 mg (1740 μmol) sodium are dissolved in 1.2 ml dry ethanol and added dropwise to the first solution, the mixture is stirred overnight at RT, then separated by RP-HPLC.

Workup

  1. additionadded dropwise to the first solution
  2. customseparated by RP-HPLC

Sources & evidence

ORD record
ord-b52039f514be4f0c96c55fe171f7369b
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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