Benzoic Acid → N-Phenethylbenzamide

HRID 1065736Notes

Reaction equation

HRID 1065736 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10](O)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N1CCOCC1)C>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][NH:9][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 1001PhenethylamineHCID 7525Ethylmorpholine

Product 1

HCID 95083N-Phenethylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

17.6 Grams of a 50% solution of n-propane-phosphonic acid anhydride in methylene chloride are added in 3 portions, with stirring and the exclusion of moisture, to a solution of 2.4 g of β-phenylethylamine, 2.2 g of benzoic acid and 14 ml of N-ethyl morpholine in 25 ml of methylene chloride. The temperature rises to about +40° C. The mixture is cooled to room temperature, while stirring, and is worked up after 24 hours of standing by adding 350 ml of methylene chloride and extracting the solution three times with 50 ml each of water, saturated sodium carbonate solution and potassium bisulfate solution. The crude product crystallizes from the methylene chloride solution dried over magnesium sulfate. Said product is filtered off with suction together with a small amount of petroleum ether (boiling point 40° to 60° C.).

Workup

  1. customrises to about +40° C
  2. stirringwhile stirring
  3. extractionextracting the solution three times with 50 ml each of water, saturated sodium carbonate solution and potassium bisulfate solution
  4. customThe crude product crystallizes from the methylene chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationis filtered off with suction together with a small amount of petroleum ether (boiling point 40° to 60° C.)

Sources & evidence

ORD record
ord-0883e297f56c4808b8652d7d5ba36b75
Source dataset
uspto-grants-1982_05
Patent number
US04331592

Reaction notes

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