Benzoyl chloride → HCID 13335991, compound

HRID 979988Notes

Reaction equation

HRID 979988 reaction equation
C([O-])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[Cl:11][C:12]1[CH:28]=[C:16]([C:17]([O:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:18])[C:15]([OH:29])=[C:14]([C:30](=[O:33])[CH2:31][CH3:32])[CH:13]=1.[C:34](Cl)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>>[Cl:11][C:12]1[CH:13]=[C:14]2[C:15](=[C:16]([C:17]([O:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]3)=[O:18])[CH:28]=1)[O:29][C:32]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[C:31]([CH3:34])[C:30]2=[O:33]

Participants

5

Reactant 4

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 517055Sodium BenzoateHCID 13335984HCID 13335984, compound

Product 1

HCID 13335991HCID 13335991, compoundYield 83%

Procedure

A 14.4 g (0.1 mole) quantity of sodium benzoate was added with stirring to a mixture of 10.2 g (0.03 mole) of β-piperidinoethyl 5-chloro-3-propionylsalicylate and 12.6 g (0.09 mole) of benzoyl chloride. The resulting mixture was heated in an oil bath at 180° to 190° C. for 8 hours to undergo reaction. After cooling, a 5% aqueous solution of sodium carbonate was added to the reaction mixture. The solids formed were purified with alcohol to provide 10.6 g (83.0%) of white crystals which were treated with a hydrochloric acid-alcohol mixture and were recrystallized from alcohol. The hydrochloride of the compound was found to have a melting point of 196.1° to 198.3° C.

Workup

  1. temperatureThe resulting mixture was heated in an oil bath at 180° to 190° C. for 8 hours
  2. customreaction
  3. temperatureAfter cooling
  4. customThe solids formed
  5. customwere purified with alcohol

Sources & evidence

ORD record
ord-003a8e5cb8ff47ef98796906abbd207a
Source dataset
uspto-grants-1987_01
Patent number
US04634768

Reaction notes

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