Triphosgene → 8-bromo-3-cyclopropylquinazoline-2,4(1H,3H)-dione

HRID 1056123Notes

Reaction equation

HRID 1056123 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[C:25]([Br:26])=[CH:24][CH:23]=[CH:22][C:15]=1[C:16]([NH:18][CH:19]1[CH2:21][CH2:20]1)=[O:17]>C(Cl)Cl>[Br:26][C:25]1[CH:24]=[CH:23][CH:22]=[C:15]2[C:14]=1[NH:13][C:2](=[O:4])[N:18]([CH:19]1[CH2:20][CH2:21]1)[C:16]2=[O:17]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 825474772-amino-3-bromo-N-cyclopropylbenzamide

Product 1

HCID 897937858-bromo-3-cyclopropylquinazoline-2,4(1H,3H)-dioneYield 249.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphosgene (Sigma-Aldrich; 2.79 g, 9.41 mmol) was added to a solution of 2-amino-3-bromo-N-cyclopropylbenzamide (723a; 6.00 g, 23.52 mmol) in DCM (235 mL) at RT. The mixture was heated to reflux and stirred overnight (17 h). The mixture turned cloudy upon heating. The next morning the reaction mixture was cooled and concentrated to afford 8-bromo-3-cyclopropylquinazoline-2,4(1H,3H)-dione (723b; 6.61 g, 23.51 mmol, 100% yield) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.09 (d, J=8.02 Hz, 1H), 8.06 (br. s., 1H), 7.78 (dd, J=7.82, 1.17 Hz, 1H), 7.10 (t, J=7.92 Hz, 1H), 2.74-2.84 (m, 1H), 1.21 (q, J=7.04 Hz, 2H), 0.83-0.91 (m, 2H). m/z (ES, +ve) 281.0, 283.0 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureupon heating
  4. temperatureThe next morning the reaction mixture was cooled
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-290713c796e54822b48a4832f1f513ed
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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