Sodium Hydroxide → Salclobuzate Sodium

HRID 2374106Notes

Reaction equation

HRID 2374106 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:7])=[C:4]([OH:17])[CH:3]=1.[OH-].[Na+:19]>C(O)(C)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([O-:14])=[O:13])=[O:7])=[C:4]([OH:17])[CH:3]=1.[Na+:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 98815804-(4-Chloro-2-hydroxybenzamido)butanoic acid

Product 1

HCID 23664294Salclobuzate SodiumYield 92%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

A one liter, four neck round bottom flask was equipped with an overhead stirrer, reflux condenser, thermocouple temperature read out, and heating mantle. The following reaction was run under a dry nitrogen atmosphere. Isopropanol (400 mL) and 4-[(4-chloro-2-hydroxy-benzoyl)amino]butanoic acid (25.0 g, 0.09 mol) were charged to the reactor and stirring was started. The reaction slurry was heated to 50° C. until a hazy brown solution was obtained. The warm solution was filtered through a warm pressure filter dressed with Whatman #1 paper into a clean 1 L reactor. The clear yellow filtrate was heated to 62° C. while stirring. Sodium hydroxide solution (50% aqueous; 7.2 g, 0.09 mol) was charged to the reactor while maintaining vigorous agitation. After the base addition was complete, the reactor was heated to reflux (72° C.) and then allowed to cool slowly to ambient temperature. The product was isolated by vacuum filtration through a sintered glass funnel and vacuum dried at 50° C. for 24 hours to give 23.16 g of sodium 4-[(4-chloro-2-hydroxybenzoyl)amino]butanoate as an off-white solid. The yield was 92%.

Workup

  1. customA one liter, four neck round bottom flask was equipped with an overhead stirrer
  2. temperaturereflux condenser
  3. temperatureheating mantle
  4. customThe following reaction
  5. customwas obtained
  6. filtrationThe warm solution was filtered through a warm pressure
  7. filtrationfilter
  8. customdressed with Whatman #1 paper into a clean 1 L reactor
  9. temperatureThe clear yellow filtrate was heated to 62° C.
  10. stirringwhile stirring
  11. temperaturewhile maintaining vigorous agitation
  12. additionAfter the base addition
  13. temperaturethe reactor was heated
  14. temperatureto reflux (72° C.)
  15. temperatureto cool slowly to ambient temperature
  16. customThe product was isolated by vacuum filtration through a sintered glass funnel
  17. customvacuum dried at 50° C. for 24 hours

Sources & evidence

ORD record
ord-9088d80cd4db4d0d90455ab69f6d438b
Source dataset
uspto-grants-2008_12
Patent number
US07462368B2

Reaction notes

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