Sulfur → Fluproquazone

HRID 1075302Notes

Reaction equation

HRID 1075302 reaction equation
[CH:1]([N:4]1[CH:13]2[CH:8]([CH2:9][CH2:10][C:11]([CH3:14])=[CH:12]2)[C:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[N:6][C:5]1=[O:22])([CH3:3])[CH3:2].[S]>C1C2C(CCCC2)CCC1.C1(C)C=CC=CC=1>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:14])[CH:12]=2)[C:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[N:6][C:5]1=[O:22])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 5362487SulfurHCID 20494720HCID 20494720, compound

Product 1

HCID 38503Fluproquazone

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7044DecalinSolvent

Procedure

17.4 g 1-isopropyl-4-(4-fluorophenyl)-7-methyl-4a,5,6,8a-tetrahydro-2(1H)-quinazolinone are dissolved under heating in 50 ml decaline and treated portionwise at 140° with 4 g powdered sulphur. On completion of the addition stirring is continued for 1 hour at 160°. The mixture is diluted with toluene and extracted several times with 15% hydrochloric acid. The acidic phase is treated with methylene chloride and neutralized under ice cooling with sodium hydroxide solution. The water phase is extracted with methylene chloride and the combined methylene chloride extracts concentrated in vacuo. The concentrate is chromatographed on silica gel using dichloromethane and methanol as eluant. After recrystallisation from toluene the title compound is obtained, m.p. 174°-176°.

Workup

  1. additiontreated portionwise at 140° with 4 g
  2. additionOn completion of the addition
  3. extractionextracted several times with 15% hydrochloric acid
  4. additionThe acidic phase is treated with methylene chloride and neutralized under ice cooling with sodium hydroxide solution
  5. extractionThe water phase is extracted with methylene chloride
  6. concentrationthe combined methylene chloride extracts concentrated in vacuo
  7. customThe concentrate is chromatographed on silica gel
  8. customAfter recrystallisation from toluene the title compound
  9. customis obtained

Sources & evidence

ORD record
ord-8ac7b3ca34b04198ba0b69402f46bc29
Source dataset
uspto-grants-1983_07
Patent number
US04395550

Reaction notes

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