Acetic Acid → HCID 15524159, compound

HRID 369483Notes

Reaction equation

HRID 369483 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19].[CH2:20]1[O:22][CH2:21]1.[C:23](O)(=[O:25])[CH3:24]>O>[OH:25][CH2:23][CH2:24][N:1]([CH2:21][CH2:20][OH:22])[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6354Ethylene OxideHCID 15524158HCID 15524158, compound

Product 1

HCID 15524159HCID 15524159, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4-amino-3-(2'-(2"-methoxyethoxy)ethoxy)benzoate (5.0 g, 18.6 mmol) and ethylene oxide (8.8 g, 200 mol) were dissolved in 150 mL acetic acid to form a reaction mixture. The mixture was stirred at room temperature for 12 hours. It was diluted with 300 mL H2O, extracted with chloroform/methanol (95/5, 4×200 mL). The organic solution was concentrated to form methyl 4-bis(2'-hydroxyethyl)amino-3-(2'-(2"-methoxyethoxy)ethoxy)benzoate as an off-white oil (6.1 g, 92%). 1H NMR (300 MHz, CDCl3): 7.62 (dd, J=8.1, 2.1 Hz, 1H), 7.52 (d, J=2.1 Hz, 1H), 7.05 (d, J=7.2 Hz, 1H), 4.22 (m, 4H), 3.89 (s, 3H, 3.9-3.8 (m, 4H), 3.68 (m, 6H), 3.58 (m, 2H), 3.38 (m, 2H), 3.37 (s, 1H). ESMS calcd (C17H27NO7): 357.2; found: 358.3 (M+H)+.

Workup

  1. customto form a reaction mixture
  2. extractionextracted with chloroform/methanol (95/5, 4×200 mL)
  3. concentrationThe organic solution was concentrated

Sources & evidence

ORD record
ord-2ed78d6401904b03b672890729d193fc
Source dataset
uspto-grants-2000_10
Patent number
US06137003

Reaction notes

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