m-Chloroperbenzoic acid → HCID 22478277, compound

HRID 1838591Notes

Reaction equation

HRID 1838591 reaction equation
[Cl:1]C1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:36]=[CH:35][C:16]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([S:30][CH2:31][CH2:32][O:33][CH3:34])=[C:25]([O:28][CH3:29])[CH:26]=3)[N:21]=[CH:20][N:19]=2)=[C:15]([F:37])[CH:14]=1>C(Cl)Cl>[ClH:1].[Cl:12][C:13]1[CH:36]=[CH:35][C:16]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([S:30]([CH2:31][CH2:32][O:33][CH3:34])=[O:9])=[C:25]([O:28][CH3:29])[CH:26]=3)[N:21]=[CH:20][N:19]=2)=[C:15]([F:37])[CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18753417HCID 18753417, compound

Product 1

HCID 22478277HCID 22478277, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Chloroperbenzoic acid (188 mg, 1.05 mmol) was added in portions to a solution of 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-methoxyethylthio)quinazoline (275 mg, 0.7 mmol), (prepared as described in Example 11), in methylene chloride (6 ml). The mixture was stirred for 30 minutes at ambient temperature, diluted with methylene chloride (20 ml), washed with aqueous sodium hydrogen carbonate solution and then brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/acetone (8/2 followed by 7/3 and 6/4). The purified product was dissolved in methylene chloride and 3M ethereal hydrogen chloride (0.5 ml) was added. The mixture was diluted with ether and the resulting precipitate was collected by filtration, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-methoxyethylsulphinyl)quinazoline hydrochloride (100 mg 38%).

Workup

  1. washwashed with aqueous sodium hydrogen carbonate solution
  2. dry with materialbrine, dried (MgSO4)
  3. customthe solvent removed by evaporation
  4. customThe residue was purified by column chromatography
  5. washeluting with methylene chloride/acetone (8/2 followed by 7/3 and 6/4)
  6. dissolutionThe purified product was dissolved in methylene chloride
  7. addition3M ethereal hydrogen chloride (0.5 ml) was added
  8. additionThe mixture was diluted with ether
  9. filtrationthe resulting precipitate was collected by filtration
  10. washwashed with ether
  11. customdried under vacuum

Sources & evidence

ORD record
ord-8459c24416cc415dabbf29ef8c117877
Source dataset
uspto-grants-2004_01
Patent number
US06673803B2

Reaction notes

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