Phosgene → HCID 13851228, compound

HRID 978432Notes

Reaction equation

HRID 978432 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH3:5][CH:6]([CH2:11][NH:12][CH3:13])[C:7]([O:9][CH3:10])=[O:8]>C1(C)C=CC=CC=1>[CH3:13][N:12]([CH2:11][CH:6]([C:7]([O:9][CH3:10])=[O:8])[CH3:5])[C:1]([Cl:4])=[O:2]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 13129055Methyl 2-methyl-3-(methylamino)propanoate

Product 1

HCID 13851228HCID 13851228, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of 16 g of phosgene in 70 ml of toluene, a solution of 17.4 g of methyl 2-methyl-3-methylaminopropionate in 30 ml of toluene was added dropwise with stirring at 20° C. The mixture was stirred at room temperature for 4 hours and evaporated to dryness. The residue was stirred for 10 min. with 100 ml of ethyl ether, filtered, the filtrates are evaporated to dryness and the residue was distilled at high vacuum to give the N-methyl-N-(2-methoxycarbonylpropyl)carbamoyl chloride, bp. 97°-100°/1 mm Hg.

Workup

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. customevaporated to dryness
  3. stirringThe residue was stirred for 10 min. with 100 ml of ethyl ether
  4. filtrationfiltered
  5. customthe filtrates are evaporated to dryness
  6. distillationthe residue was distilled at high vacuum

Sources & evidence

ORD record
ord-2cf52846814d4a6ba210646c8996e18a
Source dataset
uspto-grants-1987_05
Patent number
US04665087

Reaction notes

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