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

HRID 83776Notes

Reaction equation

HRID 83776 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

Procedure

(4-Isocyanatophenoxy)-acetic acid methyl ester 4 (15 g, 72.46 mmol) was added to ethylene glycol (30 ml) at room temperature. The reaction was exothermic and the temperature rose to 42° C. Later the reaction mixture was stirred at room temperature for 16 hours. Water (100 ml) was added and crude 5 was filtered, dried and purified by column chromatography on silica gel using chloroform as eluant to get pure 5 (16.17 g, 82.9%) as an off-white powder with an m.p between 85.5-87.5° C.

Workup

  1. customrose to 42° C
  2. filtrationcrude 5 was filtered
  3. customdried
  4. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9d4d5832ec874d0cbf3ee8c2d8389377
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Reaction notes

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