Water → HCID 10420600, compound

HRID 976107Notes

Reaction equation

HRID 976107 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:13])[NH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.O.[OH-].[Li+].[CH3:17]C1C=CC(S(C)(=O)=O)=CC=1.O>O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:13])[N:7]([CH3:17])[C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 18521p-Tolyl methyl sulfoneHCID 168937Lithium hydroxide, monohydrateHCID 1354625797-chloro-2-methylquinazolin-4-ol

Product 1

HCID 10420600HCID 10420600, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.96 g (5.0 mmol) of 7-chloro-2-methyl-4(3H)-quinazolinone and 0.20 g (4.8 mmol) of lithium hydroxide monohydrate in 25 ml of tetrahydrofuran is heated at reflux with stirring for 0.5 h. After cooling to room temperature, 0.89 g (4.8 mmol) of methyl p-toluene sulfonate is added and the reaction mixture heated at reflux for 4 hours. The reaction mixture is neutralized with con. HCl and the solvent removed in vacuo to give a residue. The residue is slurried with 50 ml of water, filtered, washed with 50 ml of 0.5M sodium hydroxide, followed by (3×50 ml) of water. The solid is dried to give 0.73 g (73%) of the desired product, m.p. 162°-165° C. None of the isomeric O-alkylated product is detected by HPLC.

Workup

  1. temperatureis heated
  2. temperatureat reflux
  3. temperaturethe reaction mixture heated
  4. temperatureat reflux for 4 hours
  5. customHCl and the solvent removed in vacuo
  6. customto give a residue
  7. filtrationfiltered
  8. washwashed with 50 ml of 0.5M sodium hydroxide
  9. customThe solid is dried

Sources & evidence

ORD record
ord-6aaefe35e9f542879f27a9b5759d4ace
Source dataset
uspto-grants-1997_03
Patent number
US05610301

Reaction notes

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