2-Propenoic acid, 2-[(methoxycarbonyl)amino]-, methyl ester → Methyl alpha-isocyanatoacrylate
Reaction equation
C[O:2][C:3]([NH:5][C:6](=[CH2:11])[C:7]([O:9][CH3:10])=[O:8])=O>C1(C)C=CC=CC=1>[N:5]([C:6](=[CH2:11])[C:7]([O:9][CH3:10])=[O:8])=[C:3]=[O:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
The apparatus and procedure used in Example 6 are repeated except that the tube is filled with silica-alumina (Strem, 87% silica, 52.39 g after drying). A solution of methyl alpha-(methoxycarbonylamino)-acrylate (5.86 g, 0.37 mmol) in 10 ml toluene is passed down the column. Both traps are cooled to -78° C., and the contents are combined for analysis. 1H NMR of the reaction products (14.2 g including toluene) indicated a 90% conversion of starting material and a 50% yield of isocyanate.
Workup
- additionis filled with silica-alumina (Strem, 87% silica, 52.39 g after drying)
Sources & evidence
- ORD record
- ord-da4e094d1f0149c6b8346c6e5b6db774
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04734453
Reaction notes
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