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

HRID 38696

Reaction equation

HRID 38696 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>[CH2:4]([N:3]([CH2:1][CH3:2])[C:20]([Cl:22])=[O:21])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

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 (1.9M in toluene; 2.4 mL, 4.6 mmol) was added over 5 minutes, and the reaction was stirred at room temperature overnight. The mixture was concentrated, and the residue was diluted with diethyl ether (150 mL) and washed twice with H2O. The organic layer was dried and concentrated to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with diethyl ether (150 mL)
  3. washwashed twice with H2O
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ba028587e25a48428392e51037537357
Source dataset
uspto-grants-2013_09
Patent number
US08524748B2

Linked notes

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