Acetyl chloride → 5-Acetoxy-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazoline

HRID 22019Notes

Reaction equation

HRID 22019 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]2[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[NH:13][C:12](=[O:20])[N:11]2[CH:21]=1.[H-].[Na+].[C:24](Cl)(=[O:26])[CH3:25]>CN(C=O)C.C(OCC)(=O)C>[C:24]([N:13]1[C:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=2[C:10]2=[N:9][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[CH:21][N:11]2[C:12]1=[O:20])(=[O:26])[CH3:25].[C:24]([O:20][C:12]1[N:11]2[CH:21]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[N:9]=[C:10]2[C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[N:13]=1)(=[O:26])[CH3:25]

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 152840972-(2-Fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazolin-5(6H)-one

Product 2

HCID 193675705-Acetoxy-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazolineHCID 19367582HCID 19367582, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(2-Fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazolin-5(6H)-one (283 mg) and 50% sodium hydride (144 mg) in DMF (5 mL) was stirred at room temperature for 15 min. Acetyl chloride (1 mL) was added and stirring was continued for 30 min. The reaction was diluted with ethyl acetate and washed with water. After drying over magnesium sulfate, the solvent was removed in vacuo and he residue was subjected to flash chromatography on silica gel with 30% ethyl acetate in hexane as the eluent to afford 6-Acetyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazolin-5(6H)-one (Compound 47) and 5-Acetoxy-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazoline (Compound 48) as white solids.

Workup

  1. stirringstirring
  2. waitwas continued for 30 min
  3. washwashed with water
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe solvent was removed in vacuo and he residue

Sources & evidence

ORD record
ord-57916de5572f40a7bd30d5c50c59fcb5
Source dataset
uspto-grants-1995_06
Patent number
US05426186

Reaction notes

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