Phosgene → 3-Benzyloxy-5,6,7,8-tetrafluoro-1H-quinazoline-2,4-dione

HRID 2270244Notes

Reaction equation

HRID 2270244 reaction equation
[NH2:1][C:2]1[C:18]([F:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]([F:22])[C:3]=1[C:4]([NH:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5].[C:23](Cl)(Cl)=[O:24]>O1CCOCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:8]([O:7][N:6]1[C:4](=[O:5])[C:3]2[C:2](=[C:18]([F:19])[C:17]([F:20])=[C:16]([F:21])[C:15]=2[F:22])[NH:1][C:23]1=[O:24])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 6371PhosgeneHCID 226328792-Amino-N-benzyloxy-3,4,5,6-tetrafluoro-benzamide

Product 1

HCID 226328803-Benzyloxy-5,6,7,8-tetrafluoro-1H-quinazoline-2,4-dioneYield 51%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-amino-N-benzyloxy-3,4,5,6-tetrafluoro-benzamide (Example V-3, 1.72 g, 5.47 mmol) in 1,4-dioxane (50 mL) was reacted with a 20% solution of phosgene (4.25 mL, 8.00 mmol) in toluene and heated to 80° C. in a sealed tube for 18 hours. The mixture was then cooled, diluted with ethyl acetate, and washed with saturated aqueous NaHCO3. The organic layer was dried with magnesium sulfate and concentrated. The residue was triturated with diethyl ether and filtered to provide 0.95 g of the title compound as a solid.

Workup

  1. temperatureThe mixture was then cooled
  2. washwashed with saturated aqueous NaHCO3
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was triturated with diethyl ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-05129559f87342548745dad6af4887b2
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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