Sulfanilamide → 4-[(8-Bromo-6-fluoro-2-quinazolinyl)amino]benzenesulfonamide

HRID 2079636Notes

Reaction equation

HRID 2079636 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:13])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[N:8]=[CH:7]2.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1.C(OCC)(=O)C>C(O)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([F:13])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:22])=[O:23])=[CH:17][CH:16]=1)[N:8]=[CH:7]2

Participants

5

Reactant 3

HCID 5333SulfanilamideHCID 8857Ethyl AcetateHCID 591992998-Bromo-2-chloro-6-fluoroquinazoline

Product 1

HCID 250162634-[(8-Bromo-6-fluoro-2-quinazolinyl)amino]benzenesulfonamideYield 81%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

To a 0.4M suspension of 8-bromo-2-chloro-6-fluoroquinazoline in isopropanol was added 4-aminobenzensulfonamide (1 eq). The reaction mixture was heated to 120° C. in an oil bath for 2 days. LCMS showed that reaction was complete under the condition. Ethyl acetate was added to the reaction flask and the suspension was stirred at ambient temperature for 30 min and was filtered. Filter cake was rinsed with hexane and dried in vacuum to give product in 81% yield. ES/MS m/z 397/399 (MH+).

Workup

  1. customLCMS showed that reaction
  2. filtrationwas filtered
  3. filtrationFilter cake
  4. washwas rinsed with hexane
  5. customdried in vacuum
  6. customto give product in 81% yield

Sources & evidence

ORD record
ord-23d7a533e393465fa320ea2cc31c2812
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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