Sulfur → Ciproquazone

HRID 2166558Notes

Reaction equation

HRID 2166558 reaction equation
[CH:1]1([CH2:4][N:5]2[C:14]3[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=3)[CH:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:7][C:6]2=[O:23])[CH2:3][CH2:2]1.[S]>ClC1C=CC=CC=1Cl>[CH:1]1([CH2:4][N:5]2[C:14]3[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=3)[C:8]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[N:7][C:6]2=[O:23])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 5362487SulfurHCID 131890501-cyclopropylmethyl-4-phenyl-6-methoxy-3,4-dihydro-2(1H)-quinazolinone

Product 1

HCID 36489CiproquazoneYield 88.2%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of 1.54 g of 1-cyclopropylmethyl-4-phenyl-6-methoxy-3,4-dihydro-2(1H)-quinazolinone, 0.48 g of sulfur and 10 ml of o-dichlorobenzene was stirred under reflux for 5 hours. The solvent was then removed under reduced pressure, and the residue was treated with hot acetone. The insoluble sulfur was filtered off and the filtrate was concentrated to dryness. The residue was recrystallized from toluene to give 1.35 g of 1-cyclopropylmethyl-4-phenyl-6-methoxy-2(1H)-quinazolinone, m.p. 114°-115° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. customThe solvent was then removed under reduced pressure
  3. additionthe residue was treated with hot acetone
  4. filtrationThe insoluble sulfur was filtered off
  5. concentrationthe filtrate was concentrated to dryness
  6. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-2643f18b3a3247edb13b4389eee9b889
Source dataset
uspto-grants-1983_06
Patent number
US04387223

Reaction notes

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