Oxalyl chloride → Benzofuro[3,2-d]pyrimidine-2,4(1H,3H)-dione

HRID 1408466Notes

Reaction equation

HRID 1408466 reaction equation
[NH2:1][CH:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH:3]1[C:11]([NH2:13])=[O:12].C(Cl)(=O)[C:15](Cl)=[O:16]>C1(C)C=CC=CC=1>[NH:1]1[C:2]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[O:4][C:3]=2[C:11](=[O:12])[NH:13][C:15]1=[O:16]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 66988222HCID 66988222, compound

Product 1

HCID 12353989Benzofuro[3,2-d]pyrimidine-2,4(1H,3H)-dioneYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

To a stirred solution of 3-amino-2,3-dihydrobenzofuran-2-carboxamide (82.2 mg, 0.461 mmol, 1.0 eq.) in anhydrous toluene (8 mL) under an inert atmosphere was added oxalyl chloride (70.2 mg, 553 μmol, 1.2 eq.) in a dropwise manner. The resulting mixture was heated to reflux (115° C.) for 4 hours whereupon it was cooled and stirred for a further 16 hours. The crude reaction mixture was concentrated to half of its volume and filtered to give a colorless solid (41.5 mg, 45%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperaturewas cooled
  3. customThe crude reaction mixture
  4. concentrationwas concentrated to half of its volume
  5. filtrationfiltered

Sources & evidence

ORD record
ord-d5c02217c7884951bb6adf80a3ddd063
Source dataset
uspto-grants-2014_12
Patent number
US08921361B2

Reaction notes

Loading…