Methyl Acrylate → HCID 118022928, compound
Reaction equation
[C:1](OC)(=O)[CH:2]=[CH2:3].Cl.Cl.[NH:9]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[NH2:10].[O-]CC.[Na+].P(Cl)(Cl)([Cl:23])=O.[OH-].[Na+]>O.CO.ClCCl.C(O)C>[Cl:23][C:1]1[CH2:2][CH2:3][N:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:10]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 20 °C
Procedure
A 500 mL, 3-neck round bottom flask was charged with methyl acrylate (18.9 g, 220 mmol) and ethanol (110 mL). 3-hydrazinopyridine dihydrochloride (20.0 g, 110 mmol) was added, followed by sodium ethoxide (29.9 g, 439 mmol) and the reaction was stirred at 60° C. for 6 hours, at which point thin layer chromatography (TLC) analysis [Eluent: 10% methanol/dichloromethane] indicated that the starting material had disappeared and a major product had formed: ESIMS m/z 164 ([M+H]+). The reaction was allowed to cool to 20° C. and concentrated to afford a yellow solid. The resulting solid was charged with phosphoryl chloride (100 g, 654 mmol). The reaction was stirred at 60° C. for 3 hours, at which point a sample of the reaction mixture was diluted with water and basified with 15 wt % sodium hydroxide (NaOH) solution. The resulting solution was extracted with ethyl acetate (EtOAc) and the organic layer was analyzed by thin layer chromatography [Eluent: ethyl acetate], which indicated that the reaction was complete.
Workup
- customa major product had formed
- concentrationconcentrated
- customto afford a yellow solid
- extractionThe resulting solution was extracted with ethyl acetate (EtOAc)
Sources & evidence
- ORD record
- ord-3055782c6a6143eea25829c419f2aaea
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09414594B2
Reaction notes
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