Acetyl chloride → HCID 15233092, compound

HRID 1770002Notes

Reaction equation

HRID 1770002 reaction equation
[OH:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[S:14].[Na].[C:16](Cl)(=[O:18])[CH3:17]>C(Cl)Cl>[C:16]([O:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[S:14])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 5360545SodiumHCID 13217988HCID 13217988, compound

Product 1

HCID 15233092HCID 15233092, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A slurry of 6.00 g (0.0260 mole) of 1-hydroxy-3-methyl-2-thioxo-1,2-dihydroquinazoline-4(3H)-one, sodium salt (IIa-Na) in 48 ml of methylene chloride was added to 2.1 g (0.0265 mole) of acetyl chloride at reflux. After 5 minutes, the colorless solution developed a white precipitate. After 1 hour at reflux, the reaction was cooled, filtered and the solvent was removed in vacuo to give 6.50 g of the crude product. The product was then recrystallized from 55 ml of methylene chloride and 150 ml of petroleum ether to give 4.62 g of compound IIi. The yield was 94.6%. Compound IIj-IIl were made in a similiar manner to compound IIi by using the appropriate acid chlorides and compound IIa-Na.

Workup

  1. temperatureat reflux
  2. temperatureAfter 1 hour at reflux
  3. temperaturethe reaction was cooled
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customto give 6.50 g of the crude product
  7. customThe product was then recrystallized from 55 ml of methylene chloride and 150 ml of petroleum ether

Sources & evidence

ORD record
ord-3de2760a18314d16b5f0b99e02c63f6a
Source dataset
uspto-grants-1995_01
Patent number
US05384405

Reaction notes

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