Phosgene → N-ethyl-N-(oxan-4-yl)carbamoyl chloride

HRID 650868Notes

Reaction equation

HRID 650868 reaction equation
[CH2:1]([NH:3][CH:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)[CH3:2].C(N(CC)CC)C.[C:17](Cl)([Cl:19])=[O:18]>ClCCl>[CH2:1]([N:3]([CH:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)[C:17]([Cl:19])=[O:18])[CH3:2]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 10964527N-ethyltetrahydro-2H-pyran-4-amine

Product 1

HCID 11127103N-ethyl-N-(oxan-4-yl)carbamoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At −30° C., a solution of 19 g (0.15 mol) of ethyl(tetrahydro-2H-pyran-4-yl)amine and 14.8 g (0.15 mol) of triethylamine in 10 ml of dichloromethane was slowly added dropwise to a solution of 44 g (0.44 mol) of phosgene in 100 ml of dichloromethane. The mixture was slowly warmed to room temperature (over a period of approximately 3 hours) and then heated under reflux for 30 minutes, excess phosgene was removed using a nitrogen stream, and the solution was concentrated. 200 ml of hexane were added, the solids were filtered off and the filtrate was concentrated. Yield 25.3 g. MS (m/z): 192 [M+H]+, 156 [M−Cl]+.

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 30 minutes
  3. customexcess phosgene was removed
  4. concentrationthe solution was concentrated
  5. addition200 ml of hexane were added
  6. filtrationthe solids were filtered off
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a343d04a3acf4550a40c78d21f6971be
Source dataset
uspto-grants-2001_08
Patent number
US06277790B1

Reaction notes

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