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

HRID 563684Notes

Reaction equation

HRID 563684 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-2fabad5641c5426cae656d4326331fa4
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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