Pyridine → N-[2,6-Bis (1-methylethyl)phenyl]-2-(9H-xanthen-9-yl)acetamide

HRID 864872Notes

Reaction equation

HRID 864872 reaction equation
[CH:1]1[C:14]2[CH:13]([CH2:15][C:16](O)=[O:17])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[CH3:25][CH:26]([C:28]1[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]([CH3:37])[CH3:36])[C:29]=1[NH2:30])[CH3:27].N1C=CC=CC=1>ClCCl.CN(C)C=O>[CH3:37][CH:35]([C:31]1[CH:32]=[CH:33][CH:34]=[C:28]([CH:26]([CH3:27])[CH3:25])[C:29]=1[NH:30][C:16](=[O:17])[CH2:15][CH:13]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:6][C:5]2[C:14]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH3:36]

Participants

7

Reactant 4

HCID 1049PyridineHCID 32484DiisopropylanilineHCID 65578Oxalyl chlorideHCID 8346622-(9H-xanthen-9-yl)acetic acid

Product 1

HCID 15345962N-[2,6-Bis (1-methylethyl)phenyl]-2-(9H-xanthen-9-yl)acetamideYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 51 mg (0.21 mmol) of 2-(9H-xanthen-9yl)acetic acid in 2 ml of dichloromethane were added 0.1 ml (1.1 mmol) of oxalyl chloride and one drop of N,N-dimethylformamide with ice-cooling, and the resulting mixture was stirred for 3 hours and freed from the solvent and an excess of the reagent by distillation under reduced pressure. The residue was again dissolved in 2 ml of dichloromethane, and 93 mg (0.53 mmol) of 2,6-bis(1-methylethyl)aniline and 0.2 ml of pyridine were added thereto with ice-cooling, followed by stirring at room temperature for 5 hours. After distilling off the solvent, the residue thus obtained was purified by column chromatography through 15 g of silica gel using a 30:0-1 mixture of dichloromethane and ethyl acetate as an eluent to give 78 mg (92%) of the desired compound as crystals.

Workup

  1. temperaturecooling
  2. distillationan excess of the reagent by distillation under reduced pressure
  3. dissolutionThe residue was again dissolved in 2 ml of dichloromethane
  4. temperaturewith ice-cooling
  5. stirringby stirring at room temperature for 5 hours
  6. distillationAfter distilling off the solvent
  7. customthe residue thus obtained
  8. customwas purified by column chromatography through 15 g of silica gel using
  9. additiona 30:0-1 mixture of dichloromethane and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-d0f62166217a459d8a76d9e019b6b18a
Source dataset
uspto-grants-1996_10
Patent number
US05563169

Reaction notes

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