Water → HCID 89793967, compound

HRID 1056409Notes

Reaction equation

HRID 1056409 reaction equation
[NH2:1][C:2]1[C:14]([Br:15])=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6][CH:7]1[CH2:10][CH2:9][CH2:8]1)=[O:5].Cl[C:17](Cl)([O:19]C(=O)OC(Cl)(Cl)Cl)Cl.O>C(Cl)Cl>[Br:15][C:14]1[CH:13]=[CH:12][CH:11]=[C:3]2[C:2]=1[NH:1][C:17](=[O:19])[N:6]([CH:7]1[CH2:8][CH2:9][CH2:10]1)[C:4]2=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 94429TriphosgeneHCID 89782174HCID 89782174, compound

Product 1

HCID 89793967HCID 89793967, compoundYield 326.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-amino-3-bromo-N-cyclobutylbenzamide (2.127 g, 7.90 mmol) and triphosgene (0.797 g, 2.69 mmol) in DCM (80 mL) was heated at reflux (using a water-cooled reflux condenser) for 17 h. The reaction mixture was then concentrated in vacuo, and the residue was taken up in toluene (80 mL) and heated at 110° C. for 1.5 h. Additional triphosgene (0.040 g, 014 mmol) was added, and the resulting solution was stirred at 110° C. for 45 min. The reaction mixture was then cooled to RT and concentrated in vacuo to give crude 8-bromo-3-cyclobutylquinazoline-2,4(1H,3H)-dione (2.59 g, 8.78 mmol) as a light-yellow solid. m/z (ESI, +ve) 295.0/297.0 (M+H)+. This material was used directly in the subsequent transformation.

Workup

  1. temperaturewas heated
  2. temperatureat reflux (
  3. temperaturecooled
  4. temperaturereflux condenser) for 17 h
  5. concentrationThe reaction mixture was then concentrated in vacuo
  6. additionAdditional triphosgene (0.040 g, 014 mmol) was added
  7. temperatureThe reaction mixture was then cooled to RT
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-168d4d2076cd4fa9b27ec8298d35808c
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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