Potassium cyanate → 5-Methyl-2-(3-nitrophenyl)-1,2-dihydro-3H-1,2,4-triazol-3-one
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][N:11]=[CH:12][CH3:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[O-:14][C:15]#[N:16].[K+].Cl[O-].[Na+]>C(O)(=O)C.O>[CH3:13][C:12]1[NH:16][C:15](=[O:14])[N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:11]=1Participants
Conditions
- Temperature
- 20 °C
Procedure
To a stirred, warm (40° C.) solution of 66.2 g (0.37 mole) of acetaldehyde 3-nitrophenylhydrazone (compound 40, FIG. 5) in one liter of acetic acid was added a solution of 30.0 g (0.37 mole) of potassium cyanate in 75 ml of water. The reaction mixture was cooled to 20° C. and stirred for 30 minutes. An aqueous 5% sodium hypochlorite solution (600 ml) was added to the mixture during a 30 minute period while maintaining a temperature of 20° C. A precipitate formed during the addition. After this addition was complete, the mixture was diluted with one liter of water and was filtered; the filtrate was saved for further use. The filter cake was triturated with a solution of ethyl acetate:n-heptane (1:1) and was filtered. The solid thus collected was dried under reduced pressure to yield 52.4 g of 4,5-dihydro-3-methyl-1-(3-nitrophenyl)-1,2,4-triazol-5(1H)-one.
Workup
- temperaturewhile maintaining a temperature of 20° C
- customA precipitate formed during the addition
- additionAfter this addition
- filtrationwas filtered
- customThe filter cake was triturated with a solution of ethyl acetate:n-heptane (1:1)
- filtrationwas filtered
- customThe solid thus collected
- customwas dried under reduced pressure
Sources & evidence
- ORD record
- ord-1794bd09d13c428fbb205467dfded6bb
- Source dataset
- uspto-grants-1990_12
- Patent number
- US04980480
Reaction notes
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