2,6-Dimethylaniline → (2,6-Dimethyl-phenyl)-carbamic acid propyl ester

HRID 1820122Notes

Reaction equation

HRID 1820122 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].Cl[C:11]([O:13][CH2:14][CH2:15][CH3:16])=[O:12]>C(#N)C>[CH2:14]([O:13][C:11](=[O:12])[NH:4][C:3]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=1[CH3:1])[CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 68962,6-DimethylanilineHCID 7998Propyl chloroformate

Product 1

HCID 5140633(2,6-Dimethyl-phenyl)-carbamic acid propyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

2,6-Dimethyl-aniline (3.0 mL) and propyl chloroformate (4.1 mL) were dissolved in acetonitrile (15 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. The reaction mixture was concentrated in vacuo to furnish 4.79 g (95% yield) of the title compound as a brown solid. The crude product was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-498c8d01d20740549eae36566caee0a3
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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