Reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[NH:10][NH2:11].[OH-].[Na+].C(O[CH:17]=[C:18]([C:21]#[N:22])[C:19]#[N:20])C>CCOC(C)=O>[NH2:22][C:21]1[N:10]([C:4]2[C:3]([Cl:2])=[CH:8][CH:7]=[CH:6][C:5]=2[Cl:9])[N:11]=[CH:17][C:18]=1[C:19]#[N:20]Participants
Conditions
- Temperature
- 0 °C
Procedure
(2,6-Dichlorophenyl)hydrazine hydrochloride (5 g, 23.42 mmol) was partitioned between EtOAc (100 mL) and NaOH (2M, aq) (40 mL). The organic layer separated and washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and concentrated. The resultant oil was suspended in methanol (50 mL) under nitrogen at −5° C. 2-(Ethoxymethylene)malononitrile (2.86 g, 23.42 mmol) added portionwise over 5 mins and the mixture stirred at 0° C. for 30 mins. The reaction mixture was allowed to warm to room temperature and then heated at reflux under nitrogen for 2 hours. The reaction mixture was allowed to cool and evaporated to dryness to afford the product (5.60 g, 94%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 4.47 (2H, s), 7.43-7.47 (1H, m), 7.51-7.53 (2H, m), 7.73 (1H, s); m/z (ES+) (M+H)+=253; HPLC tR=1.62 min.
Workup
- customThe organic layer separated
- washwashed with water (50 mL), brine (50 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customwas suspended in methanol (50 mL) under nitrogen at −5° C
- temperatureto warm to room temperature
- temperatureheated
- temperatureat reflux under nitrogen for 2 hours
- temperatureto cool
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-1a364376c0094c1da210d6ca661f6ea5
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143263B2
Linked notes
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