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

HRID 36683

Reaction equation

HRID 36683 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:4][CH2:5][CH3:6])=[O:3])[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 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 at room temperature for a further 2 hours, the organic phase is separated off, the aqueous phase is extracted with toluene and the toluene solutions are dried over K2CO3. The solution is concentrated and the residue is distilled.

Workup

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

Sources & evidence

ORD record
ord-acd54b968634414ab260eeadb9f96832
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Linked notes

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