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

HRID 2197369Notes

Reaction equation

HRID 2197369 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-84abd6d411274728ab62e52aac036336
Source dataset
uspto-grants-2012_12
Patent number
US08338484B2

Reaction notes

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