Phosgene → N-methyl-N-(2-ethoxycarbonyl-4-phenylbutyl)carbamoyl chloride

HRID 978430Notes

Reaction equation

HRID 978430 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH3:5][NH:6][CH2:7][CH:8]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10]>C1(C)C=CC=CC=1>[CH3:5][N:6]([CH2:7][CH:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:1]([Cl:4])=[O:2]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 12491965HCID 12491965, compound

Product 1

HCID 13851227N-methyl-N-(2-ethoxycarbonyl-4-phenylbutyl)carbamoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 10.3 g of phosgene in 45 ml of toluene, the solution of 20.3 g of ethyl 2-methylaminomethyl-4-phenylbutyrate (described in example 1) in 19 ml of toluene was added over a period of 20 minutes. The mixture was stirred at room temperature for 4 hours and evaporated to dryness. The residue was stirred for 10 minutes with 100 ml of ether, the solids were filtered, the filtrates were evaporated to dryness and the residue was distilled under high vacuum to give N-methyl-N-(2-ethoxycarbonyl-4-phenylbutyl)carbamoyl chloride, bp 179°-189°/1 mm Hg.

Workup

  1. customevaporated to dryness
  2. stirringThe residue was stirred for 10 minutes with 100 ml of ether
  3. filtrationthe solids were filtered
  4. customthe filtrates were evaporated to dryness
  5. distillationthe residue was distilled under high vacuum

Sources & evidence

ORD record
ord-9514e2975b0c4ab5a2e649e868e1e1bd
Source dataset
uspto-grants-1987_05
Patent number
US04665087

Reaction notes

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