Phosgene → 6-Chloroquinazoline-2,4(1H,3H)-dione

HRID 1648216

Reaction equation

HRID 1648216 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([NH2:9])=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1.[C:12](Cl)(Cl)=[O:13]>O1CCCC1>[Cl:1][C:2]1[CH:10]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:11][C:12](=[O:13])[NH:9][C:7]2=[O:8]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 788762-Amino-5-chlorobenzamide

Product 1

HCID 3039986-Chloroquinazoline-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloroanthranilamide (3.4 g)in tetrahydrofuran (50 mL) was added phosgene (16 mL, 1.93M solution in toluene) via an addition funnel. The reaction mixture was stirred at room temperature for 4 hours and then heated to reflux for another two hours. The reaction mixture was concentrated to a total volume about 10 mL. After cooling, the title compound (3.72 g) having the following physical data, was collected by filtration and dried in vacuum.

Workup

  1. temperatureheated
  2. temperatureto reflux for another two hours
  3. concentrationThe reaction mixture was concentrated to a total volume about 10 mL
  4. temperatureAfter cooling
  5. filtrationwas collected by filtration
  6. customdried in vacuum

Sources & evidence

ORD record
ord-6c47f84f579245e3a259b7c032951650
Source dataset
uspto-grants-1995_07
Patent number
US05436233

Linked notes

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