Phosgene → Carbamic chloride, N-ethyl-N-(phenylmethyl)-

HRID 1920009Notes

Reaction equation

HRID 1920009 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:2].C(N(C(C)C)CC)(C)C.[C:20](Cl)([Cl:22])=[O:21]>C(Cl)Cl>[CH2:1]([N:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:20]([Cl:22])=[O:21])[CH3:2]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 84352N-Ethylbenzylamine

Product 1

HCID 10679448Carbamic chloride, N-ethyl-N-(phenylmethyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-Ethylbenzylamine (0.56 mL, 3.8 mmol) and diisopropylethylamine (1 mL, 5.7 mmol) were combined in CH2Cl2 (12 mL) and cooled to 0° C. Phosgene (20% in toluene; 2.4 mL, 4.6 mmol) was added, and the reaction was stirred overnight at room temperature. The mixture was concentrated, and the residue was dissolved in Et2O and washed twice with H2O. The organic layer was dried, filtered, and concentrated to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in Et2O
  3. washwashed twice with H2O
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4fe8b39801024d59a74910a796e09768
Source dataset
uspto-grants-2012_05
Patent number
US08168678B2

Reaction notes

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