Salicylamide → HCID 23344619, compound

HRID 1856365Notes

Reaction equation

HRID 1856365 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH:11](O)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[C:12]1([CH:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:7]2[CH:8]=[C:2]([C:1]([NH2:10])=[O:9])[C:3]([OH:4])=[CH:5][CH:6]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 5147SalicylamideHCID 6101p-Toluenesulfonic acidHCID 7037Benzhydrol

Product 1

HCID 23344619HCID 23344619, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 25 g (0.182 mol) of salicylamide, 30 g (0.163 mol) of benzhydrol, 30 g (0.158 mol) of p-toluenesulfonic acid and 200 ml of acetic acid was refluxed for 3 hours with heating. After cooling, the precipitated white crystals were separated by filtration and washed with water to obtain 5-diphenylmethylsalicylamide. Thereafter 40 g of sodium hydroxide in 100 ml of water were added and the mixture was heated on a steam bath for 6 hours with stirring. After being allowed to cool, the mixture was acidified using diluted hydrochloric acid to obtain 40 g of a crude product comprising 5-diphenylmethylsalicylic acid, Compound (2). When the crude product was recrystallized using diluted methanol, it had a melting point of 190° to 191.5° C. The resulting Compound (2) was converted into the zinc salt by the same process as that described in Synthesis Example 2.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperaturewith heating
  3. temperatureAfter cooling
  4. customthe precipitated white crystals were separated by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-6d8e710cd9a8475d9944ba85eb2b6640
Source dataset
uspto-grants-1980_08
Patent number
US04219219

Reaction notes

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