Sodium hydride → Proquazone

HRID 1075299Notes

Reaction equation

HRID 1075299 reaction equation
[H-].[Na+].[CH:3]([N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:16])[CH:14]=2)[C:9](=O)[NH:8][C:7]1=[O:18])([CH3:5])[CH3:4].[H][H].[C:21]1([Mg]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1.O>[CH:3]([N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:16])[CH:14]=2)[C:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:8][C:7]1=[O:18])([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 13061754HCID 13061754, compoundHCID 178418255HCID 178418255, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 31508Proquazone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1.8 g sodium hydride in 25 ml tetrahydrofurane are added portionwise 13.08 g 1-isopropyl-7-methyl-quinazolin-2,4(1H,3H)-dione under constant release of hydrogen. 40 ml of a 2N solution of phenylmagnesiumbromide in tetrahydrofurane are added dropwise at 40° C. to the clear solution and the resulting suspension stirred at 40° for 15 hours. Water is added and the solvent is evaporated in vacuo. The residue is taken up with methylene chloride and 30 ml 12% hydrochloric acid. The organic layer is concentrated to give the title compound (recrystallized from toluene), m.p. 140°-143°.

Workup

  1. customthe solvent is evaporated in vacuo
  2. concentrationThe organic layer is concentrated

Sources & evidence

ORD record
ord-4609b38c685a4b229706e34472730ad9
Source dataset
uspto-grants-1983_07
Patent number
US04395550

Reaction notes

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