Toluene → N-Cyanoacetylethylcarbamate

HRID 68537

Reaction equation

HRID 68537 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

HCID 1140TolueneHCID 5641Carbamic acid, ethyl esterHCID 9740Cyanoacetic acidHCID 24813Phosphorus oxychloride

Product 1

HCID 23112N-CyanoacetylethylcarbamateYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

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

  1. temperatureAfter cooling
  2. customto quench phosphorus oxychloride
  3. filtrationThe reaction is filtered by suction
  4. washThe filtered cake was washed with ethyl ether
  5. customdried

Sources & evidence

ORD record
ord-710c1d615b944b7f9adc6d68cc7a8ce0
Source dataset
uspto-grants-2014_09
Patent number
US08822465B2

Linked notes

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