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

HRID 1591663Notes

Reaction equation

HRID 1591663 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-dd832533dd2d43deb4e651745db78f28
Source dataset
uspto-grants-2007_11
Patent number
US07291622B2

Reaction notes

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