2-(4-Chlorophenoxy)ethylamine → Ethyl{[({2-[(4-chlorophenyl)oxy]ethyl}-amino)carbonyl]oxy}acetate

HRID 2116594Notes

Reaction equation

HRID 2116594 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.C1([O:18][C:19]([O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=O)C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH2:10][NH:11][C:19]([O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:18])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 27941912-(4-Chlorophenoxy)ethylamineHCID 12094709Ethyl [(phenoxycarbonyl)oxy]acetate

Product 1

HCID 91288841Ethyl{[({2-[(4-chlorophenyl)oxy]ethyl}-amino)carbonyl]oxy}acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.6 g (3.5 mmol) of [(4-chloro-phenyl)oxy]ethylamine (Chim. Ther. 1973, 8, 259-270) and 1.3 g (5.8 mmol) of ethyl [(phenyloxy-carbonyl)oxy]acetate, prepared in Step 1.1., in 30 ml of toluene is heated at 60° C. overnight. It is evaporated to dryness and the product is purified by chromatography on silica gel, eluting with a 30/70 mixture of ethyl acetate and cyclohexane. This gives 0.7 g of oily product, containing ˜10% of cyclized oxazolidine dione product, used as it is in the following step.

Workup

  1. customIt is evaporated to dryness
  2. customthe product is purified by chromatography on silica gel
  3. washeluting with a 30/70 mixture of ethyl acetate and cyclohexane
  4. additionThis gives 0.7 g of oily product, containing ˜10% of cyclized oxazolidine dione product

Sources & evidence

ORD record
ord-ed6b8fecc7394dd98990156476ad2dc3
Source dataset
uspto-grants-2008_10
Patent number
US07439257B2

Reaction notes

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