Diphenylamine → HCID 86634498, compound

HRID 2080914Notes

Reaction equation

HRID 2080914 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7])#[CH:2].[C:12]1([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([N:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])#[CH:2]

Participants

4

Reactant 2

HCID 11487DiphenylamineHCID 200388133-Ethynylbenzoyl chloride

Product 1

HCID 86634498HCID 86634498, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Air in a 20 ml Schlenk tube was replaced by Ar gas and 1.02 g (7 mmol) of m-ethynylbenzoic acid and 5 g (42 mmol) of thionyl chloride were added to the tube and the mixture was stirred at 50° C. for 2 hours and then excess thionyl chloride was removed by distillation under reduced pressure to obtain m-ethynylbenzoyl chloride. To the m-ethynylbenzoyl chloride obtained was added a solution having 2.44 g (14.4 mmol) of diphenylamine dissolved in 7 ml of dichloromethane under ice-cooling and then the resultant mixture was stirred at room temperature for one hour. After completion of the stirring, dichloromethane was removed by distillation under reduced pressure and 35 ml of water was added to the resultant residue. The mixture was extracted with 35 ml of ethyl acetate, the extract was dried over magnesium sulfate and the solvent was removed by distillation under reduced pressure using an evaporator. The resultant crude reaction product was purified by column chromatography (hexane/AcOEt10/1) using silica gel to obtain 0.7 g of 3-ethynyl-N,N-diphenylbenzamide which is a desired product as pale yellow liquid. (Yield: 35%)

Workup

  1. additionwas added a solution
  2. temperaturecooling
  3. customAfter completion of the stirring, dichloromethane was removed by distillation under reduced pressure and 35 ml of water
  4. additionwas added to the resultant residue
  5. extractionThe mixture was extracted with 35 ml of ethyl acetate
  6. dry with materialthe extract was dried over magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customan evaporator
  9. customThe resultant crude reaction product
  10. customwas purified by column chromatography (hexane/AcOEt10/1)

Sources & evidence

ORD record
ord-90389f3c90e44679aad10908ef81f4fc
Source dataset
uspto-grants-2011_04
Patent number
US07932398B2

Reaction notes

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