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

HRID 2079629Notes

Reaction equation

HRID 2079629 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[N:8]=[CH:7]2.[S:17]([NH2:27])(=[O:26])([C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)=[O:18]>CC(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:25][C:22]1[CH:23]=[CH:24][C:19]([S:17]([NH2:27])(=[O:18])=[O:26])=[CH:20][CH:21]=1)[N:8]=[CH:7]2

Participants

4

Reactant 2

HCID 5333SulfanilamideHCID 59199251HCID 59199251, compound

Product 1

HCID 250160044-[[8-Bromo-6-(trifluoromethyl)-2-quinazolinyl]amino]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
110 °C

Procedure

To a 0.30 M solution of 8-bromo-2-chloro-6-(trifluoromethyl)quinazoline in 2-propanol was added sulfanilamide (1.0 eq). The reaction was stirred at 110° C. for 14 h. The hydrochloride was collected by vacuum filtration and then stirred in aqueous sodium bicarbonate. The solid was collected by vacuum filtration and rinsed with water. The light yellow solid was dried in a desiccator to give 343 mg of the desired product. ES/MS m/z 447, 449 (MH+).

Workup

  1. filtrationThe hydrochloride was collected by vacuum filtration
  2. stirringstirred in aqueous sodium bicarbonate
  3. filtrationThe solid was collected by vacuum filtration
  4. washrinsed with water
  5. customThe light yellow solid was dried in a desiccator

Sources & evidence

ORD record
ord-0ded3928daca4d30a4e71ee1571a8a08
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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