Potassium Cyanide → HCID 23458556, compound
Reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]3[CH:15]([C:16](=[O:19])[NH:17][N:18]=2)[CH2:14]3)=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cu][C:27]#[N:28].[C-]#N.[K+]>O.Cl.C1(C)C=CC=CC=1>[C:27]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]3[CH:15]([C:16](=[O:19])[NH:17][N:18]=2)[CH2:14]3)=[CH:8][CH:7]=1)#[N:28]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
A cold solution of 2.4 g (34.8 millimoles) of sodium nitrite in 20 ml of water is added to a solution of 7.0 g (34.8 millimoles) of 2-(p-aminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one (see Example 8a) in 26 ml of concentrated hydrochloric acid and 260 ml of water whilst stirring at 0° C. The mixture is then stirred for a further 10 minutes, at 0°-5° C., after which it is neutralized with sodium carbonate at the same temperature. The resulting solution is added dropwise, whilst stirring, to a cold (0°-5° C.) solution of 3.9 g (43.5 millimoles) of copper-(I) cyanide and 7.0 g (107.5 millimoles) of potassium cyanide in 175 ml of water, covered with a layer of 85 ml of toluene. The mixture is then stirred for 30 minutes at 5° C., followed by 20 hours at room temperature. After filtering off the product and drying it under reduced pressure at 50° C., 6.6 g (90% of theory) of 2-(p-cyanophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one are obtained as brown crystals, of melting point 265°-266° C. after recrystallization from acetonitrile.
Workup
- stirringThe mixture is then stirred for a further 10 minutes, at 0°-5° C.
- additionThe resulting solution is added dropwise
- stirringThe mixture is then stirred for 30 minutes at 5° C.
- filtrationAfter filtering off the product
- customdrying it under reduced pressure at 50° C.
Sources & evidence
- ORD record
- ord-e03c864002634d199dce250f2c8c4f4e
- Source dataset
- uspto-grants-1981_06
- Patent number
- US04271163
Reaction notes
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