Hydrochloric Acid → HCID 13066642, compound

HRID 1606632Notes

Reaction equation

HRID 1606632 reaction equation
C([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](Cl)=[O:8])(=O)C.[NH2:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([NH2:24])[CH:23]=1)[C:18]([OH:20])=[O:19].[C:25]([O-:28])(=O)[CH3:26].[K+].Cl>O1CCOCC1.O>[C:5]([NH:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([NH:24][C:7](=[O:8])[C:6]2[C:5](=[CH:13][CH:12]=[CH:11][CH:10]=2)[OH:4])[CH:23]=1)[C:18]([OH:20])=[O:19])(=[O:4])[C:6]1[C:25](=[CH:26][CH:12]=[CH:11][CH:10]=1)[OH:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 120623,5-Diaminobenzoic acidHCID 796682-Acetoxybenzoyl chlorideHCID 517044Potassium Acetate

Product 1

HCID 13066642HCID 13066642, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 17.5 g of 2-acetoxybenzoylchloride in 20 ml of dioxane was added at one time to a mixture of 4.6 g of 3,5-diaminobenzoic acid, 15.3 g of potassium acetate and 80 ml of water while stirring at a temperature of from 0° to 5°C. The stirring was continued at that temperature for one hour, then at room temperature for 30 minutes and at 50°C for 30 minutes. The resulting reaction mixture was added to 200 ml of cold diluted hydrochloric acid and the undissolved substance was separated. The substance was dissolved in about 100 ml of 1N NaOH aqueous solution and then the solution was treated with active carbon and acidified with hydrochloric acid so as to bring the pH of the solution to 3 - 4 thereby precipitating crystals. The crystals were recovered by filtration and washed with water. Recrystallization from methanol-water gave 7.2 g of 3,5-bis(salicylamido)-benzoic acid having a melting point between 305° - 108°308°(decomposition).

Workup

  1. waitat room temperature for 30 minutes
  2. waitat 50°C for 30 minutes
  3. customThe resulting reaction mixture
  4. customthe undissolved substance was separated
  5. dissolutionThe substance was dissolved in about 100 ml of 1N NaOH aqueous solution
  6. additionthe solution was treated with active carbon
  7. customthereby precipitating crystals
  8. filtrationThe crystals were recovered by filtration
  9. washwashed with water
  10. customRecrystallization from methanol-water

Sources & evidence

ORD record
ord-ae6539132a71433ca6a649fc3abf87f0
Source dataset
uspto-grants-1976_04
Patent number
US03953496

Reaction notes

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