Acetic Acid → 6,7-Dihydro-6-p-methoxybenzylthiO-5H-pyrrolo[2,1-c]-1,2,4-triazole
Reaction equation
C(O[C:4]1[CH2:8][CH:7]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:6][N:5]=1)C.[CH:19]([NH:21][NH2:22])=O.C(O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C(OCC)(=O)C>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][S:9][CH:7]2[CH2:6][N:5]3[C:4](=[N:22][N:21]=[CH:19]3)[CH2:8]2)=[CH:16][CH:15]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2-ethoxy-4-p-methoxybenzylthio-1-pyrroline (1.06 g) in ethanol (50 ml) there was added 0.36 g of formylhydrazine and heated to 80° C under argon atmosphere while stirring. After 1.5 hours, 0.24 g of formylhydrazine was further added and stirred under heating for 30 minutes at the same temperature. Then, 0.6 g of acetic acid was added, stirred for 30 minutes at that temperature and then cooled to room temperature. To the cooled product were added ethyl acetate and 5% aqueous solution of sodium carbonate to dis&ribute the product between these two liquids. The resulting organic phase was washed with saturated NaCl aqueous solution, dried over Na2SO4 and distilled off the solvent under reduced pressure to obtain the objective product.
Workup
- stirringstirred
- temperatureunder heating for 30 minutes at the same temperature
- stirringstirred for 30 minutes at that temperature
- temperaturecooled to room temperature
- washThe resulting organic phase was washed with saturated NaCl aqueous solution
- dry with materialdried over Na2SO4
- distillationdistilled off the solvent under reduced pressure
- customto obtain the objective product
Sources & evidence
- ORD record
- ord-ffad41102065460da57e2b2c928e3780
- Source dataset
- uspto-grants-1990_10
- Patent number
- US04962202
Reaction notes
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