Water → N,3-diphenylprop-2-ynamide

HRID 1623434Notes

Reaction equation

HRID 1623434 reaction equation
[C:1]1([NH2:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]1([C:14]#[C:15][C:16](O)=[O:17])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(N=C=NC2CCCCC2)CCCCC1.O>ClCCl>[C:1]1([NH:7][C:16](=[O:17])[C:15]#[C:14][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 10868DicyclohexylcarbodiimideHCID 69475Phenylpropiolic Acid

Product 1

HCID 305965N,3-diphenylprop-2-ynamideYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenylamine (1.86 g, 20 mmol) and phenylpropiolic acid (3.22 g, 22 mmol) were dissolved in dichloromethane (50 ml) and 1,3-dicyclohexylcarbodiimide (4.8 g, 23.2 mmol) was added in one portion at 0° C. The mixture was stirred room temperature for 14 h. The mixture was poured into water and extracted with dichloromethane (3×15 ml). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash column chromatography on silica gel, eluting with hexanes-EtOAc (6:1 and then 4:1) afforded 3-phenyl-propynoic acid phenylamide 2.7 g (62%).

Workup

  1. extractionextracted with dichloromethane (3×15 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by flash column chromatography on silica gel
  5. washeluting with hexanes-EtOAc (6:1

Sources & evidence

ORD record
ord-94f3c604df584ba9a3828719b8f43fcf
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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