Phosgene → Ethyl 2-aminoacetate isocyanate

HRID 2412317Notes

Reaction equation

HRID 2412317 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[C:9](Cl)(Cl)=[O:10]>C(#N)C.N1C=CC=CC=1>[N-:7]=[C:9]=[O:10].[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3]

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 2723640Glycine ethyl ester, hydrochloride2×

Product 1

HCID 86647037Ethyl 2-aminoacetate isocyanate

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

Alternatively, glycine ethyl ester hydrochloride (35.7 g, 0.256 mole) was suspended in dry acetonitrile (300 ml) containing phosgene (50.7 g, 0.512 mole) and the reaction mixture was refluxed. A few drops of dry pyridine was added after 1 hr. of refluxing. Unreacted glycine ethyl ester hydrochloride was filtered off and dry toluene (300 ml) was added then acetonitrile was distilled off. The toluene solution was refluxed for 1 hr. to obtain glycine ethyl ester isocyanate (IR 2250 cm-1). This isocyanate was reacted, without further purification, with anhydrous methanol.

Workup

  1. temperaturethe reaction mixture was refluxed
  2. temperatureof refluxing
  3. filtrationwas filtered off
  4. additiondry toluene (300 ml) was added
  5. distillationacetonitrile was distilled off
  6. temperatureThe toluene solution was refluxed for 1 hr

Sources & evidence

ORD record
ord-517b9ee87c714842bec381454690c64b
Source dataset
uspto-grants-1985_01
Patent number
US04491548

Reaction notes

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