Triethylamine → 4-Methoxybenzyl(2-methoxyethyl)carbamoyl chloride

HRID 2212962Notes

Reaction equation

HRID 2212962 reaction equation
ClC([O:4][C:5]([Cl:8])(Cl)Cl)=O.[CH3:9][O:10][C:11]1[CH:22]=[CH:21][C:14]([CH2:15][NH:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[CH3:9][O:10][C:11]1[CH:22]=[CH:21][C:14]([CH2:15][N:16]([CH2:17][CH2:18][O:19][CH3:20])[C:5]([Cl:8])=[O:4])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 32858732-methoxy-N-(4-methoxybenzyl)ethanamine

Product 1

HCID 219560334-Methoxybenzyl(2-methoxyethyl)carbamoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.51 g (0.31 ml, 2.56 mmol) of trichloromethyl chloroformate (“diphosgene”) are dissolved in 15 ml of dichloromethane, and 1.00 g (5.12 mmol) of 4-methoxybenzyl(2-methoxyethyl)amine and 0.78 g (7.68 mmol) of triethylamine are slowly added. After stirring at room temperature overnight, the mixture is poured into ice-water and extracted three times with dichloromethane, and the organic phase is dried over magnesium sulfate and concentrated to dryness in a rotary evaporator. The crude product is employed without workup directly in the next stage.

Workup

  1. extractionextracted three times with dichloromethane
  2. dry with materialthe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated to dryness in a rotary evaporator

Sources & evidence

ORD record
ord-18912abb5e604afb8af2d2a4c934ad19
Source dataset
uspto-grants-2006_09
Patent number
US07105523B2

Reaction notes

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