Sodium Hydroxide → HCID 19851971, compound

HRID 1607156Notes

Reaction equation

HRID 1607156 reaction equation
C[O:2][C:3](=[O:33])[C:4]([NH:6][C:7]1[C:12]([Cl:13])=[CH:11][C:10]([CH3:14])=[C:9]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[CH3:27])=[C:22]([OH:29])[C:21]=2[CH2:30][CH2:31][CH3:32])[CH:8]=1)=[O:5].[OH-].[Na+]>CO>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([O:19][CH2:18][CH2:17][CH2:16][O:15][C:9]2[CH:8]=[C:7]([NH:6][C:4](=[O:5])[C:3]([OH:33])=[O:2])[C:12]([Cl:13])=[CH:11][C:10]=2[CH3:14])=[C:21]([CH2:30][CH2:31][CH3:32])[C:22]=1[OH:29])(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54364491HCID 54364491, compound

Product 1

HCID 19851971HCID 19851971, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 6.1 g (12.8 mmol) of N-{3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-4-methyl-6-chlorophenyl}-oxamic acid methyl ester in 200 ml of methanol and 14.1 ml of N sodium hydroxide solution is heated under reflux for 90 minutes. The reaction mixture is concentrated under reduced pressure, dissolved in hot water and, after cooling, acidified with dilute hydrochloric acid. The product that has formed is filtered off, washed with water and recrystallised from acetone. N-{3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-4-methyl-6-chlorophenyl}-oxamic acid having a melting point of 183°-184° (decomposition) is obtained. The acid is dissolved in 350 ml of acetone, and one equivalent of triethanolamine is added thereto. The solution is concentrated under reduced pressure to approximately one third and ether is added. The product that has formed is filtered off and washed with ether. The triethanolammonium salt of N-{3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-4-methyl-6-chlorophenyl}-oxamic acid having a melting point of 70° (decomposition) is obtained.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 90 minutes
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. dissolutiondissolved in hot water
  5. temperatureafter cooling
  6. customThe product that has formed
  7. filtrationis filtered off
  8. washwashed with water
  9. customrecrystallised from acetone

Sources & evidence

ORD record
ord-6b97f92cf8b24796b2411d1d33fc48dc
Source dataset
uspto-grants-1989_09
Patent number
US04863942

Reaction notes

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