Triphosgene → 3-(3-bromo-2-methylphenyl)-7-fluoroquinazoline-2,4(1H,3H)-dione

HRID 523226Notes

Reaction equation

HRID 523226 reaction equation
[NH2:1][C:2]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[C:8]=1[CH3:14])=[O:5].Cl[C:21](Cl)([O:23]C(=O)OC(Cl)(Cl)Cl)Cl.C([O-])(O)=O.[Na+]>C1COCC1>[Br:13][C:9]1[C:8]([CH3:14])=[C:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:18][C:17]([F:19])=[CH:16][CH:15]=3)[NH:1][C:21]2=[O:23])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 1076239052-amino-N-(3-bromo-2-methylphenyl)-4-fluorobenzamide

Product 1

HCID 1177609783-(3-bromo-2-methylphenyl)-7-fluoroquinazoline-2,4(1H,3H)-dioneYield 106.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-amino-N-(3-bromo-2-methylphenyl)-4-fluorobenzamide (3.65 g, 11.3 mmol) in THF (50 mL) was treated with triphosgene (3.69 g, 12.4 mmol) at room temperature. The solution was stirred at room temperature for 2 h, then was treated slowly with saturated aqueous NaHCO3 and stirred until no more gas evolution was observed. The resulting mixture was extracted twice with EtOAc. The combined organic phases were washed twice with water, then with brine, dried and concentrated to give 3-(3-bromo-2-methylphenyl)-7-fluoroquinazoline-2,4(1H,3H) -dione (4.20 g), used without further purification. Mass spectrum m/z 349, 351 (M+H)+.

Workup

  1. stirringstirred until no more gas evolution
  2. extractionThe resulting mixture was extracted twice with EtOAc
  3. washThe combined organic phases were washed twice with water
  4. dry with materialwith brine, dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-18a37ba136674979bb8af1f372f1f096
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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