Sodium Hydroxide → 2-chloro-6-iodo-1H-quinazolin-4-one

HRID 2045726Notes

Reaction equation

HRID 2045726 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([I:13])[CH:8]=2)[N:3]=1.[OH-:14].[Na+]>C1COCC1.O.Cl.CCOC(C)=O>[Cl:1][C:2]1[N:11]=[C:10]([OH:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([I:13])[CH:8]=2)[N:3]=1

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 114615062,4-Dichloro-6-iodoquinazoline

Product 1

HCID 1785178192-chloro-6-iodo-1H-quinazolin-4-oneYield 100%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,4-dichloro-6-iodoquinazoline (10 g, 30.8 mmol) in THF (8 ml) and water (8 ml) was treated with aqueous NaOH (1 N, 4 ml). The solution was stirred for 1 h, then diluted with aqueous HCl (1 N) and EtOAc. The organic phase was separated and washed with brine then dried over Na2SO4. Filtration and removal of the volatiles afforded the title compound (9.4 g, 100%) as a solid. LCMS (ES+) m/z 307 (M+H)+.

Workup

  1. customThe organic phase was separated
  2. washwashed with brine
  3. dry with materialthen dried over Na2SO4
  4. filtrationFiltration and removal of the volatiles

Sources & evidence

ORD record
ord-d2a7e62e2e884784858aa414302f6853
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

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