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

HRID 2242927Notes

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

Conditions

Temperature: 60 °C

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

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

Sources & evidence

ORD record: ord-bf0fa41479ee4d4d9305882af05c6e76
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674805B2

Reaction notes

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