Water → HCID 89783973, compound

HRID 1056273Notes

Reaction equation

HRID 1056273 reaction equation
[NH2:1][C:2]1[C:13]([Br:14])=[CH:12][CH:11]=[CH:10][C:3]=1[C:4]([NH:6][CH:7]([CH3:9])[CH3:8])=[O:5].[C:15](OC(Cl)(Cl)Cl)(OC(Cl)(Cl)Cl)=[O:16].O>C(Cl)Cl>[Br:14][C:13]1[CH:12]=[CH:11][CH:10]=[C:3]2[C:2]=1[NH:1][C:15](=[O:16])[N:6]([CH:7]([CH3:9])[CH3:8])[C:4]2=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 94429TriphosgeneHCID 82547469HCID 82547469, compound

Product 1

HCID 89783973HCID 89783973, compoundYield 250%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A slurry of 2-amino-3-bromo-N-isopropylbenzamide (406a, 1.00 g, 3.89 mmol) and tri-phosgene (Aldrich; 0.462 g, 1.556 mmol) in 50 mL DCM was fitted with a water cooled reflux condenser and drying tube and heated to reflux overnight. In the morning, complete conversion to desired product. The reaction was cooled and concentrated in vacuo to give 8-bromo-3-isopropylquinazoline-2,4(1H,3H)-dione (1.1 g, 3.89 mmol, 100% yield) as a white solid: 1H NMR (400 MHz, CDCl3) δ ppm 8.02-8.25 (1H, m), 7.98 (1H, br. s.), 7.78 (1H, dd, J=7.8, 1.4 Hz), 7.11 (1H, t, J=7.9 Hz), 5.27 (1H, dt, J=13.9, 6.9 Hz), 1.56 (6H, s). m/z (ESI, +ve) 282.9/284.9 (M+H)+.

Workup

  1. temperaturecooled
  2. temperaturereflux condenser
  3. customdrying tube
  4. temperatureheated
  5. temperatureto reflux overnight
  6. temperatureThe reaction was cooled
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-111efbd42bfe4d38a19686063994723c
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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