Hydrochloric Acid → HCID 22169207, compound

HRID 843214Notes

Reaction equation

HRID 843214 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[N:10][C:11]2[CH:23]=[CH:22][C:14]([O:15][CH2:16][C:17]([O:19]CC)=[O:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+].Cl>CN(C)C=O.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]=[N:10][C:11]2[CH:23]=[CH:22][C:14]([O:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22616837HCID 22616837, compound

Product 1

HCID 22169207HCID 22169207, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1.95 g (0.006 mol) of ethyl 2-[4(4-cyanophenylazo)phenoxy]-ethanoate was dissolved in a mixture of 100 mL of dimethylformamide and 20 mL of water in a 250 mL one-neck round flask fitted with a magnetic stirring bar and a reflux condenser by heating to 90° C. while stirring on an oil bath. 1.3 g (0.033 mol) of NaOH was added. Stirring and heating were continued for ½ h. After cooling on an ice-water bath 6 mL of 6 N HCl was added. The precipitated crude product was recovered by filtration. The precipitate was suspended in a mixture of 10 mL of ethanol and 3 mL of water for 15 min. and filtered. The filtercake was washed with 10 mL of cold ethanol. After drying under vacuum overnight 1.17 g (yield 69%) of 2-[4-(4-cyanophenylazo)phenoxy]-ethanoic acid was obtained

Workup

  1. customfitted with a magnetic stirring bar and a reflux condenser
  2. stirringStirring
  3. temperatureheating
  4. additionwas added
  5. customThe precipitated crude product
  6. filtrationwas recovered by filtration
  7. additionThe precipitate was suspended in a mixture of 10 mL of ethanol and 3 mL of water for 15 min.
  8. filtrationfiltered
  9. washThe filtercake was washed with 10 mL of cold ethanol

Sources & evidence

ORD record
ord-1202842043364b4db1c39e41f472d5d1
Source dataset
uspto-grants-2002_04
Patent number
US06376655B1

Reaction notes

Loading…