Hydrochloric Acid → HCID 13066643, compound

HRID 1606633Notes

Reaction equation

HRID 1606633 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]=[CH:22][C:23]=1[NH2:24])[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]=[CH:22][C:23]=1[NH:24][C:7](=[O:8])[C:6]1[C:5](=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:4])[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 692633,4-Diaminobenzoic acidHCID 796682-Acetoxybenzoyl chloride2×HCID 517044Potassium Acetate

Product 1

HCID 13066643HCID 13066643, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 17.2 g of 2-acetoxybenzoylchloride in 20 ml of dioxane was added at one time to a mixture of 4.6 g of 3,4-diaminobenzoic acid, 15.3 g of potassium acetate and 70 ml of water while stirring at a temperature of from 0° to 5°C, followed by stirring at that temperature for 30 minutes. To the mixture was added a solution of 1 g of 2-acetoxybenzoylchloride in 3 ml of dioxane. The resulting mixture was stirred at room temperature for 30 minutes and then at 50°C for 30 minutes. The reaction mixture was added to 200 ml of cold diluted hydrochloric acid and the undissolved mixture of oil and powdery solid was separated. The mixture was dissolved in about 100 ml of 1N aqueous sodium hydroxide solution, and the solution was treated with active carbon and then acidified to precipitate crystals. The crystals were recovered by filtration and washed with water. Recrystallization from a mixture of dioxane and water gave 6.9 g of 3,4-bis(salicylamido)-benzoic acid having a melting point between 305° - 307°C (decomposition).

Workup

  1. stirringby stirring at that temperature for 30 minutes
  2. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  3. additionthe undissolved mixture of oil and powdery solid
  4. customwas separated
  5. dissolutionThe mixture was dissolved in about 100 ml of 1N aqueous sodium hydroxide solution
  6. additionthe solution was treated with active carbon
  7. customto precipitate crystals
  8. filtrationThe crystals were recovered by filtration
  9. washwashed with water
  10. customRecrystallization
  11. additionfrom a mixture of dioxane and water

Sources & evidence

ORD record
ord-6b30898f9e4b44aeb3b3194f3e61146c
Source dataset
uspto-grants-1976_04
Patent number
US03953496

Reaction notes

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