Reacción #470810

ord-6088e4455ad34cccbaed3a649b1af038

Ecuación de reacción

Nc1cccc(CO)c1
3-aminobenzyl alcohol
CCOC(=O)Cl
ethyl chloroformate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCOC(=O)Nc1cccc(CO)c1
Ethyl(3-hydroxymethylphenyl)carbamate

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturasubsequently cooled to 0° C
  2. 2
    workup.ADDITIONAfter the addition
  3. 3
    workup.STIRRINGthe reaction mixture is stirred for 20 h and at the same time
  4. 4
    Temperaturaslowly warmed to room temperature
  5. 5
    Otroformed (evolution of gas!)
  6. 6
    OtroThe organic phase is separated off
  7. 7
    Extracciónthe aqueous phase is extracted with 200 ml of dichloromethane
  8. 8
    Lavadothe combined organic phases are washed with saturated sodium chloride solution
  9. 9
    Secadodried over sodium sulfate
  10. 10
    Otrothe solvent is removed by distillation

Procedimiento

50 g (406 mmol) of 3-aminobenzyl alcohol are suspended in 750 ml of dichloromethane under a nitrogen atmosphere, the mixture is stirred at room temperature for 30 min and subsequently cooled to 0° C. 49 g (452 mmol) of ethyl chloroformate are slowly added dropwise. After the addition, the reaction mixture is stirred for 20 h and at the same time slowly warmed to room temperature. 300 ml of 1M potassium carbonate solution are added to the suspension formed (evolution of gas!). The organic phase is separated off, the aqueous phase is extracted with 200 ml of dichloromethane, the combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, and the solvent is removed by distillation.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08367668B2uspto-grants-2013_02