Acetone → HCID 54509604, compound

HRID 1579538Notes

Reaction equation

HRID 1579538 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)=[O:7])=[CH:4][CH:3]=1.CC(C)=O.Cl.[CH2:24]([NH:26][CH2:27][CH2:28][NH:29][S:30]([C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=1)(=[O:32])=[O:31])[CH3:25]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([N:26]([CH2:27][CH2:28][NH:29][S:30]([C:33]2[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=2)(=[O:32])=[O:31])[CH2:24][CH3:25])=[O:12])=[O:7])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 665642-(4'-Chlorobenzoyl)benzoic acidHCID 21568619HCID 21568619, compound

Product 1

HCID 54509604HCID 54509604, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 13 grams of ψ-acid chloride of 0-(p-chlorobenzoyl)benzoic acid in 30 ml. of acetone was added dropwise to a stirred solution of 14 grams of N-[2-(ethylamino)ethyl]-p-toluenesulfonamide hydrochloride in 100 ml. of pyridine. The solution was refluxed for 1.75 hours then the solvent was removed in vacuo. The residue dissolved in ethyl acetate and extracted successively with water, and saturated sodium carbonate solution. After drying over magnesium sulfate, the ethyl acetate was removed in vacuo. The solid was slurried with ethyl acetate and separated. On recrystallization from ethyl acetate there was obtained 2-(p-chlorobenzoyl)-N-[2-(p-toluenesulfonamido)ethyl]-N-ethylbenzamide, m.p. 145°-147°C.

Workup

  1. temperatureThe solution was refluxed for 1.75 hours
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue dissolved in ethyl acetate
  4. extractionextracted successively with water, and saturated sodium carbonate solution
  5. dry with materialAfter drying over magnesium sulfate
  6. customthe ethyl acetate was removed in vacuo
  7. customseparated
  8. customOn recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-cc0d0a952867484fa3eb43ab33c5c8dd
Source dataset
uspto-grants-1976_01
Patent number
US03931218

Reaction notes

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