Phosgene → HCID 86740864, compound

HRID 1982409Notes

Reaction equation

HRID 1982409 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH2:6].[C:12](Cl)(Cl)=[O:13]>C1(C)C=CC=CC=1>[N-:6]=[C:12]=[O:13].[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH2:6]

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 2723695Leucine methyl ester hydrochloride

Product 1

HCID 86740864HCID 86740864, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A three-neck 1 liter round bottom flask, fitted with gas inlet, mechanical stirrer, reflux condenser and gas outlet connected to a 30% aqueous NaOH trap was charged with L-leucine methyl ester hydrochloride (61.0 g, 0.336 mmol) and dry toluene (250 ml). The mixture was heated to gentle reflux for 0.5 hr. while a vigorous stream of phosgene was continuously introduced. Following dissolution of the solids (0.5 hr.) phosgene was introduced for an additional 15 min. The product was isolated by initially removing the toluene under vacuum and fractionally distilling the remaining residue under vacuum to give the product (48.0 g), bp=71°-73° C. at 0.8 torr.

Workup

  1. customA three-neck 1 liter round bottom flask, fitted with gas inlet, mechanical stirrer
  2. temperaturereflux condenser and gas outlet
  3. customconnected to a 30% aqueous NaOH trap
  4. temperatureThe mixture was heated
  5. temperatureto gentle reflux for 0.5 hr
  6. additionwas introduced for an additional 15 min
  7. customThe product was isolated
  8. customby initially removing the toluene under vacuum
  9. distillationfractionally distilling the remaining residue under vacuum

Sources & evidence

ORD record
ord-afa833b85ffa484d9deef20f20dae0b9
Source dataset
uspto-grants-1986_06
Patent number
US04596789

Reaction notes

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