Oxalyl chloride → 4-Chloroquinazoline-6,7-diyl diacetate

HRID 1797884Notes

Reaction equation

HRID 1797884 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][C:16](=[O:18])[CH3:17])[N:11]=[CH:10][NH:9][C:8]2=O)(=[O:3])[CH3:2].C(Cl)(=O)C([Cl:23])=O>C(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][C:16](=[O:18])[CH3:17])[N:11]=[CH:10][N:9]=[C:8]2[Cl:23])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 136013901HCID 136013901, compound2×

Product 1

HCID 272813774-Chloroquinazoline-6,7-diyl diacetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 6,7-diacetoxy-4(3H)-quinazolinone, 12 (3.20 g, 11.42 mmol) in CHCl3 (60 ml) was added oxalyl chloride (2.2 ml, 17.3 mmol) dropwise at 0° C. The resulting reaction mixture was stirred at room temperature for 15 minutes then was gradually heated to reflux for 5 h during which time the starting material was consumed. The reaction mixture was cooled to 10° C. and the solution was quenched with aq sodium bicarbonate. The organic layer was separated and washed with brine then dried over Na2SO4 and directly taken to the next step without concentration.

Workup

  1. customThe resulting reaction mixture
  2. temperaturethen was gradually heated
  3. temperatureto reflux for 5 h during which time the starting material
  4. customwas consumed
  5. temperatureThe reaction mixture was cooled to 10° C.
  6. customthe solution was quenched with aq sodium bicarbonate
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialthen dried over Na2SO4
  10. concentrationdirectly taken to the next step without concentration

Sources & evidence

ORD record
ord-96315d7273964b919b307acc3bd5e19a
Source dataset
uspto-grants-2013_01
Patent number
US08343950B2

Reaction notes

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