Chloride → HCID 15870875, compound

HRID 1586464Notes

Reaction equation

HRID 1586464 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=1.[Cl-].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C.O>[C:23]1([NH:22][C:16](=[O:17])[C:15]2[CH:19]=[CH:20][C:12]([O:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)=[CH:13][CH:14]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 312ChlorideHCID 6115AnilineHCID 8471TriethylamineHCID 10611637HCID 10611637, compound

Product 1

HCID 15870875HCID 15870875, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
35 °C

Procedure

Under an atmosphere of nitrogen, 53 mg (0.20 mmol) of 4-(2-naphtyloxy) benzoic acid was suspended in 5 ml of dried methylene chloride, to which were added 56 mg (0.44 mmol) of oxyalyl chloride and then 1 drop of DMF with a pipette. The mixture was stirred at 35° C. for 1.5 hours. The reaction mixture was concentrated with an evaporator, and the residue was dissolved in 5 ml of dried methylene chloride. Under an atmosphere of nitrogen, the solution, while being cooled with ice, was added dropwise to a solution of 19 mg (0.20 mmol) of aniline and of 22 mg (0.22 mmol) of triethyl amine in dried methylene chloride (5 ml), and the resulting mixture was stirred for 4 hours in an ice bath, and then stirred overnight at room temperature. Water was added to the reaction mixture, and extracted with methylene chloride twice. The organic phase was washed with brine dried with anhydrous sodium sulfate, and the solvent was removed by evaporation. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give 27 mg (40% yield) of N-phenyl-(4-(2-naphthyloxy)benzamide). White solid.

Workup

  1. concentrationThe reaction mixture was concentrated with an evaporator
  2. dissolutionthe residue was dissolved in 5 ml of dried methylene chloride
  3. temperatureUnder an atmosphere of nitrogen, the solution, while being cooled with ice
  4. stirringthe resulting mixture was stirred for 4 hours in an ice bath
  5. stirringstirred overnight at room temperature
  6. extractionextracted with methylene chloride twice
  7. washThe organic phase was washed with brine
  8. dry with materialdried with anhydrous sodium sulfate
  9. customthe solvent was removed by evaporation
  10. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-74ca469b7dee48cbaab0a7d1a265073d
Source dataset
uspto-grants-1999_08
Patent number
US05945450

Reaction notes

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