Benzyl chloroformate → Benzyl prop-2-yn-1-ylcarbamate

HRID 480346Notes

Reaction equation

HRID 480346 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].[CH2:5]([O:12][C:13](Cl)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>N1C=CC=CC=1.CCOC(C)=O>[CH2:5]([O:12][C:13](=[O:14])[NH:4][CH2:1][C:2]#[CH:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformate2×HCID 239041Propargylamine

Product 1

HCID 11137906Benzyl prop-2-yn-1-ylcarbamateYield 32.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of propargylamine (6.4 g, 71.2 mmol) in pyridine (100 mL) was added benzylchloroformate (13.37 g, 78.2 mmol) in 100 mL CH2Cl2over 0.5 h. The reaction benzylchloroformate (13.37 g, 78.2 mmol) in 100 mL CH2Cl2over0.5 h. The reaction dissolved in EtOAc and the organic solution was washed with water (2×). The organic solution was washed with dilute aqueous HCl followed by saturated NaHCO3. The organic solution was dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound (4.43 g).

Workup

  1. custom5 h
  2. washthe organic solution was washed with water (2×)
  3. washThe organic solution was washed with dilute aqueous HCl
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5558a50175844f9a696d3137caa8e02
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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