Phenacyl bromide → 1-(3'-Acetamino-phenyl)-2-(phenacyl-amino)-propane oxalate

HRID 597729Notes

Reaction equation

HRID 597729 reaction equation
[NH:1]([C:5]1[CH:6]=[C:7]([CH2:11][CH:12]([NH2:14])[CH3:13])[CH:8]=[CH:9][CH:10]=1)[C:2]([CH3:4])=[O:3].Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18].[C:25](=[O:28])([O-:27])[O-].[K+].[K+]>C(#N)C>[C:2]([OH:3])(=[O:18])[C:25]([OH:27])=[O:28].[NH:1]([C:5]1[CH:6]=[C:7]([CH2:11][CH:12]([NH:14][CH2:16][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])[CH3:13])[CH:8]=[CH:9][CH:10]=1)[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 21446209N-[3-(2-Aminopropyl)phenyl]acetamide

Product 1

HCID 213274281-(3'-Acetamino-phenyl)-2-(phenacyl-amino)-propane oxalateYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture consisting of 9.6 gm of 1-(3'-acetamino-phenyl)-2-amino-propane (see Example 2), 10 gm of α-bromoacetophenone, 7 gm of potassium carbonate and 200 ml of acetonitrile was refluxed for 3 hours. Thereafter, the inorganic precipitate which had formed was removed by suction filtration, and 5 gm of oxalic acid were added to the filtrate. The precipitate formed thereby was collected by suction filtration, yielding 6 gm of 1-(3'-acetamino-phenyl)-2-(phenacyl-amino)-propane oxalate, m.p. 136° -140° C. The oxalate was added to 60 ml of ethanolic 10% hydrochloric acid, and the mixture was refluxed for four hours. Thereafter, the reaction solution was evaporated, the residue was caused to crystallize by treating it with acetonitrile and a little water, and the crystallizate was purified by dissolving it in a little water, filtering the solution through activated charcoal, and adding acetonitrile to the filtrate. The dihydrochloride of the formula ##STR27## having a melting point of 169° -173° C (decomp.) was obtained.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThereafter, the inorganic precipitate which had formed
  3. customwas removed by suction filtration, and 5 gm of oxalic acid
  4. additionwere added to the filtrate
  5. customThe precipitate formed
  6. filtrationthereby was collected by suction filtration

Sources & evidence

ORD record
ord-c0156b424ef649508e86527cbf9f7029
Source dataset
uspto-grants-1977_03
Patent number
US04015011

Reaction notes

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