Ethyl chloroformate → Ethyl (3-hydroxymethylphenyl)carbamate

HRID 2093347Notes

Reaction equation

HRID 2093347 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].Cl[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[OH:6][CH2:5][C:4]1[CH:3]=[C:2]([NH:1][C:11](=[O:12])[O:13][CH2:14][CH3:15])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 802933-Aminobenzyl alcohol

Product 1

HCID 10607893Ethyl (3-hydroxymethylphenyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 g (406 mmol) of 3-aminobenzyl alcohol are suspended in 750 ml of dichloromethane under a nitrogen atmosphere and 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 distilled off.

Workup

  1. temperaturesubsequently cooled to 0° C
  2. additionAfter the addition
  3. stirringthe reaction mixture is stirred for 20 h and at the same time
  4. temperatureslowly warmed to room temperature
  5. customformed (evolution of gas!)
  6. customThe organic phase is separated off
  7. extractionthe aqueous phase is extracted with 200 ml of dichloromethane
  8. washthe combined organic phases are washed with saturated sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-e0c4354332b04c9380855daefa0313b5
Source dataset
uspto-grants-2013_05
Patent number
US08445489B2

Reaction notes

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