Pyridine → ({[4-(3-Bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-hydrazono}-cyano-acetyl)-carbamic acid ethyl ester
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([NH2:13])=[CH:8][C:7]=1[CH3:14].N([O-])=O.[Na+].C([N:26]([C:32](=[O:36])[CH2:33][C:34]#[N:35])[C:27]([O:29][CH2:30][CH3:31])=[O:28])C.[N:37]1C=CC=CC=1>Cl.O>[CH2:30]([O:29][C:27](=[O:28])[NH:26][C:32](=[O:36])[C:33](=[N:37][NH:13][C:9]1[CH:10]=[C:11]([CH3:12])[C:6]([O:5][C:4]2[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[C:2]([Br:1])[CH:3]=2)=[C:7]([CH3:14])[CH:8]=1)[C:34]#[N:35])[CH3:31]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of 4-(3-bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenylamine (2.0 g) of PREPARATION 2 in 6N hydrochloric acid (45 ml) at 0° C. was added dropwise a solution of sodium nitrite (560 mg) in water (1.25 ml). After stirring 30 min at 0° C., this solution was added in portions to a mixture of ethylcyanoacetylurethane (2.4 g) and pyridine (12 ml) in water (150 ml) at room temperature. The resulting solids were collected, washed with water, and dried to afford the title compound as an orange solid (1.5 g) which was used directly.
Workup
- customThe resulting solids were collected
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-6aebf91f0e024646b4d7e7690b7de2da
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06930107B2
Reaction notes
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