2-(4-Phenoxyphenoxy)ethyl ethylcarbamate → N-ethyl-N-2-(4-phenoxyphenoxy)ethoxycarbonyl-oxamic acid ethyl ester

HRID 1583765Notes

Reaction equation

HRID 1583765 reaction equation
[O:1]([C:8]1[CH:22]=[CH:21][C:11]([O:12][CH2:13][CH2:14][O:15][C:16](=[O:20])[NH:17][CH2:18][CH3:19])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[CH2:24]([O:26][C:27](=[O:31])[C:28]([OH:30])=O)[CH3:25]>C(Cl)CCl>[CH2:24]([O:26][C:27](=[O:31])[C:28]([N:17]([CH2:18][CH3:19])[C:16]([O:15][CH2:14][CH2:13][O:12][C:11]1[CH:21]=[CH:22][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][CH:10]=1)=[O:20])=[O:30])[CH3:25]

Participants

4

Reactant 2

HCID 1823662-(4-Phenoxyphenoxy)ethyl ethylcarbamateHCID 23618337Oxalic acid monoethylester chloride

Product 1

HCID 54287737N-ethyl-N-2-(4-phenoxyphenoxy)ethoxycarbonyl-oxamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

9.0 g of N-ethyl-carbamic acid-2-(4-phenoxyphenoxy)ethyl ester are dissolved in 90 ml of ethylene chloride. To this solution are added 9.6 g of oxalic acid monoethyl ester chloride, and stirring is maintained for 10 hours under mild refluxing conditions. The cooled reaction mixture is then poured into 200 ml of ice-water, and the organic phase is separated. This is washed with cold water, dried over sodium sulfate, concentrated by evaporation and taken up in dichloromethane. Chromatography on silica gel with dichloromethane as the eluant thus yields the compound of the formula ##STR6## in the form of white crystals having a m.p. of 56°-58° C.

Workup

  1. temperatureis maintained for 10 hours
  2. temperatureunder mild refluxing conditions
  3. customThe cooled reaction mixture
  4. customthe organic phase is separated
  5. washThis is washed with cold water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated by evaporation
  8. customChromatography on silica gel with dichloromethane as the eluant thus yields the compound of the formula ##STR6## in the form of white crystals

Sources & evidence

ORD record
ord-dbb256ec12ac46e6a675f898862614f3
Source dataset
uspto-grants-1985_11
Patent number
US04554290

Reaction notes

Loading…