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1,2-Dichloroethane → ethyl N-n-propoxycarbamate

HRID 1451192
Notes
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Reaction equation

HRID 1451192 reaction equation
[CH2:1]([O:4][NH2:5])[CH2:2][CH3:3].C(Cl)CCl.C(=O)([O-])[O-].[K+].[K+].Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>O>[CH2:1]([O:4][NH:5][C:17](=[O:18])[O:19][CH2:20][CH3:21])[CH2:2][CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 2768918O-propylhydroxylamine

Product 1

HCID 21475744ethyl N-n-propoxycarbamateYield 93.6%

Reagents, catalysts & solvents 1

HCID 962Water
Solvent

Procedure

22 g (197 mmol) of n-propoxyamine hydroxhloride was dissolved in 100 ml of water, and 200 ml of ethylene dichloride was added thereto. Then, 27.2 g (197 mmol) of potassium carbonate was added in several times under cooling, and then 21.3 g (196 mmol) of ethyl chloroformate was dropwise added thereto at a temperature of not higher than 10° C. After raising the temperature to room temperature, the mixture was further stirred at the same temperature for 4 hours. The ethylene dichloride layer was separated, and then the aqueous layer was extracted twice with 100 ml of chloroform. The ethylene dichloride layer and the chloroform layer were put together, and washed with a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. 27 g of ethyl N-n-propoxycarbamate was obtained by distillation under reduced pressure. Boiling point: 88° C./2.5 mmHg

Workup

  1. temperatureunder cooling
  2. customhigher than 10° C
  3. customThe ethylene dichloride layer was separated
  4. extractionthe aqueous layer was extracted twice with 100 ml of chloroform
  5. washwashed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-461cc35615614caa943066bac2505bf4
Source dataset
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05604179

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes