Potassium Carbonate → HCID 23003166, compound

HRID 396211Notes

Reaction equation

HRID 396211 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][CH2:17][C:18]#[N:19])[C:10]([CH:20]=[O:21])=[CH:9]2.C([O-])([O-])=O.[K+].[K+].S([CH2:43][N+:44]#[C-:45])(C1C=CC(C)=CC=1)(=O)=O>CO>[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][CH2:17][C:18]#[N:19])[C:10]([C:20]1[O:21][CH:45]=[N:44][CH:43]=1)=[CH:9]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 23003156HCID 23003156, compound

Product 1

HCID 23003166HCID 23003166, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-[5-(2,6-dichlorobenzyloxy)-2-formyl-indol-1-yl]butyronitrile (0.2 g, 0.52 mmol), from Example 9(b), K2CO3 (0.14 g, 1.03 mmol) and tosylmethyl isocyanide (0.11 g, 0.57 mmol) in MeOH (15 mL) was stirred at room temperature for 5 min followed by reflux for 3 h to give a clear yellow solution. The solvent was removed under reduced pressure and the resulting solid was partitioned between chloroform and water. The aqueous layer was washed with chloroform twice and the combined organic layers were washed with water, brine and dried over Na2SO4. After filtration, the yellow filtrate was concentrated to yield the desired oxazol (0.21 g, 95%) as a yellow oil. MS(ES) m/e 426.0 [M+H]+.

Workup

  1. temperatureby reflux for 3 h
  2. customto give a clear yellow solution
  3. customThe solvent was removed under reduced pressure
  4. customthe resulting solid was partitioned between chloroform and water
  5. washThe aqueous layer was washed with chloroform twice
  6. washthe combined organic layers were washed with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration
  9. concentrationthe yellow filtrate was concentrated

Sources & evidence

ORD record
ord-93052dd3fc3c40ef8fcefa1858fc79fc
Source dataset
uspto-grants-2003_08
Patent number
US06608059B1

Reaction notes

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