Toluene → Ethyl N-propargylcarbamate

HRID 1033743Notes

Reaction equation

HRID 1033743 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].C1(C)C=CC=CC=1.[OH-].[Na+].Cl[C:15]([O:17][CH2:18][CH3:19])=[O:16]>O>[CH2:1]([NH:4][C:15](=[O:16])[O:17][CH2:18][CH3:19])[C:2]#[CH:3]

Participants

6

Reactant 4

HCID 1140TolueneHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 239041Propargylamine

Product 1

HCID 12155513Ethyl N-propargylcarbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

115 g (2. 1 mol) of propargylamine is introduced into 1 1 of toluene, 91 g of sodium hydroxide dissolved in 400 ml of water are added, and 239 g (2.2 mol) of ethyl chloroformate are added dropwise at 10° C. The mixture is stirred for three hours at room temperature, the organic phase is separated off, the aqueous phase is extracted using toluene, the organic solutions are dried over magnesium sulphate and concentrated, and the concentrate is distilled.

Workup

  1. additionare added
  2. customthe organic phase is separated off
  3. extractionthe aqueous phase is extracted
  4. dry with materialthe organic solutions are dried over magnesium sulphate
  5. concentrationconcentrated
  6. distillationthe concentrate is distilled

Sources & evidence

ORD record
ord-ac4509552fda4a1b9daf428c9915a524
Source dataset
uspto-grants-1994_05
Patent number
US05312823

Reaction notes

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