Ethylene Glycol → [4-(2-Hydroxy-ethoxycarbonylamino)-phenoxy]-acetic acid methyl ester

HRID 1957836Notes

Reaction equation

HRID 1957836 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]=[C:13]=[O:14])=[CH:8][CH:7]=1.[CH2:16]([OH:19])[CH2:17][OH:18]>O>[CH3:1][O:2][C:3](=[O:15])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:18][CH2:17][CH2:16][OH:19])=[O:14])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 18918618(4-Isocyanato-phenoxy)-acetic acid methyl ester

Product 1

HCID 49764368[4-(2-Hydroxy-ethoxycarbonylamino)-phenoxy]-acetic acid methyl esterYield 82.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
42 °C

Procedure

(4-Isocyanato-phenoxy)-acetic acid methyl ester 28 (15 g, 72.46 mmol) was added to ethylene glycol (30 ml) at room temperature. The reaction was exothermic and the temperature raised to 42° C. Later the reaction mixture was stirred at room temperature for 16 hours. Water (100 ml) was added and crude 29 was filtered, dried and purified by column chromatography on silica gel using chloroform as eluant to get pure 29 (16.17 g, 82.9%) as a off-white powder. M.p: 85.5-87.5° C.

Workup

  1. filtrationcrude 29 was filtered
  2. customdried
  3. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4d0e68b9a7924dffa769b09b79c684ed
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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