Dimethylformamide → HCID 57443732, compound

HRID 1879641Notes

Reaction equation

HRID 1879641 reaction equation
[CH:1]([S:4]([C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH2:9])(=[O:6])=[O:5])([CH3:3])[CH3:2].CN(C)C=O.[H-].[Na+].[Cl:21][C:22]1[N:31]=[C:30](Cl)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1>O>[Cl:21][C:22]1[N:31]=[C:30]([NH:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 2528862,4-DichloroquinazolineHCID 126463662-(Propane-2-sulfonyl)aniline

Product 1

HCID 57443732HCID 57443732, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-(isopropylsulfonyl)aniline (450 mg) and N,N-dimethylformamide (10 mL), 55% sodium hydride in oil (200 mg) was added under ice cooling and stirred for 30 minutes, followed by addition of 2,4-dichloroquinazoline (500 mg). The reaction mixture was stirred for 30 minutes under ice cooling and further stirred overnight at room temperature. The reaction mixture was cooled on ice, diluted with water and then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1-3:1) to give 2-chloro-N-[2-(isopropylsulfonyl)phenyl]quinazoline-4-amine (0.67 g) as a light-yellow solid.

Workup

  1. additionwas added under ice cooling
  2. stirringThe reaction mixture was stirred for 30 minutes under ice cooling
  3. stirringfurther stirred overnight at room temperature
  4. temperatureThe reaction mixture was cooled on ice
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated aqueous sodium chloride
  7. dry with materialAfter drying over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1-3:1)

Sources & evidence

ORD record
ord-4b5ce3113b5c4e9baece65fc69a5c01b
Source dataset
uspto-grants-2012_11
Patent number
US08318702B2

Reaction notes

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