Hydrochloric Acid → 7-(Benzyloxy)-4-(methylsulfanyl)quinazoline

HRID 1597238Notes

Reaction equation

HRID 1597238 reaction equation
[CH3:1]I.[CH2:3]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[S:21])[NH:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].Cl>C1COCC1>[CH2:3]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([S:21][CH3:1])=[N:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178527906HCID 178527906, compound

Product 1

HCID 226493097-(Benzyloxy)-4-(methylsulfanyl)quinazolineYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl iodide (0.97 ml, 15.4 mmol) was added dropwise to a solution of 7-benzyloxy-3,4-dihydroquinazolin-4-thione (3.45 g, 12.9 mmol) in THF (13 ml) containing 1M sodium hydroxide (25.7 ml). After stirring for 30 minutes at ambient temperature, the mixture was adjusted to pH7 with 2M hydrochloric acid. After dilution with water, the solid was collected by filtration, washed with water and dried under vacuum to give 7-benzyloxy-4-methylsulphanylquinazoline (3.3 g, 92%).

Workup

  1. filtrationAfter dilution with water, the solid was collected by filtration
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-a2112b9aa42248609fc760bf73691c30
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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