Toluene → N-Cyanoacetylethylcarbamate
Reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[NH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].C1(C)C=CC=CC=1.P(Cl)(Cl)(Cl)=O>O.CN(C=O)C>[C:1]([CH2:3][C:4]([NH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6])#[N:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
2-cyanoacetic acid (85 g, 1 mol) and ethyl aminoformate (89 g, 1 mol) were added to toluene (500 mL). To the mixture was slowly added phosphorus oxychloride (45 mL, 0.5 mol), and then added DMF (5 mL). The reaction was conducted at 70° C. for 2 h. After cooling, water (500 mL) was added to the reaction solution to quench phosphorus oxychloride. The reaction is filtered by suction. The filtered cake was washed with ethyl ether and dried to produce a white solid (104 g) in a yield of 67%.
Workup
- temperatureAfter cooling
- customto quench phosphorus oxychloride
- filtrationThe reaction is filtered by suction
- washThe filtered cake was washed with ethyl ether
- customdried
Sources & evidence
- ORD record
- ord-710c1d615b944b7f9adc6d68cc7a8ce0
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822465B2
Reaction notes
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