Propyl isocyanate → Methyl 5-bromo-2-(3-propylureido)isonicotinate
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([Br:12])=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:13]([N:16]=[C:17]=[O:18])[CH2:14][CH3:15]>C(Cl)(Cl)Cl>[Br:12][C:9]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]([NH:1][C:17]([NH:16][CH2:13][CH2:14][CH3:15])=[O:18])=[N:11][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
Methyl 2-amino-5-bromoisonicotinate (100 g, 433 mmol) was dissolved in chloroform (600 mL) and placed into a 1 L sealed tube. Propyl isocyanate (122.5 mL, 1.29 mol) was then added. The reactor was heated at 55° C. for 72 h at which time the reaction was determined to be complete. The mixture was then cooled to room temperature, concentrated under reduced pressure, and the solid was dissolved in 2:1 ethyl acetate: tetrahydrofuran (3 L). This solution was washed with water (2×200 mL), and the water was back extracted with ethyl acetate (300 mL). The organic layers were then dried with sodium sulfate, filtered, and concentrated yielding 129 g (95%) of methyl 5-bromo-2-(3-propylureido)isonicotinate as a dark yellow solid.
Workup
- customsealed tube
- temperatureThe mixture was then cooled to room temperature
- concentrationconcentrated under reduced pressure
- dissolutionthe solid was dissolved in 2:1 ethyl acetate
- washThis solution was washed with water (2×200 mL)
- extractionthe water was back extracted with ethyl acetate (300 mL)
- dry with materialThe organic layers were then dried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-eb6066d292d5407eb0202de5156c363c
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08283361B2
Reaction notes
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