Ethyl chloroformate → N-(1,1-dimethoxyprop-2-yl)urethane

HRID 2255695Notes

Reaction equation

HRID 2255695 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH3:7][O:8][CH:9]([O:13][CH3:14])[CH:10]([NH2:12])[CH3:11].[OH-].[Na+]>C1(C)C=CC=CC=1.O>[CH3:7][O:8][CH:9]([O:13][CH3:14])[CH:10]([NH:12][C:2](=[O:3])[O:4][CH2:5][CH3:6])[CH3:11]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 936582,2-Dimethoxy-1-methylethylamine

Product 1

HCID 15069987N-(1,1-dimethoxyprop-2-yl)urethane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

80 g (0.73 mol) of ethyl chloroformate are added dropwise with ice-cooling to 86.2 g (0.72 mol) of 2-aminopropionaldehyde dimethyl acetal in 350 ml of toluene and 32 g (0.8 mol) of NaOH in 300 ml of water. The mixture is stirred for a further 2 hours at room temperature, the organic phase is separated off, the aqueous phase is extracted using toluene and the toluene solutions are dried over K2CO3. The extracts are concentrated and the residue is distilled.

Workup

  1. customthe organic phase is separated off
  2. extractionthe aqueous phase is extracted
  3. dry with materialthe toluene solutions are dried over K2CO3
  4. concentrationThe extracts are concentrated
  5. distillationthe residue is distilled

Sources & evidence

ORD record
ord-c45ad79cc62b455faa7900db5b5a393e
Source dataset
uspto-grants-1993_08
Patent number
US05241076

Reaction notes

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