Toluene → 3,4-dihydro-1-isopropyl-4-(3-methoxyphenyl)-7-methyl-2(1H)-quinazolinone

HRID 1834759Notes

Reaction equation

HRID 1834759 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([NH2:10])=[O:9])[CH:2]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O.[C:22]1(C)[CH:27]=CC=C[CH:23]=1.CS(O)(=O)=O>C1C=CC=CC=1>[CH:22]([N:7]1[C:3]2[C:4](=[CH:5][CH:6]=[C:1]([CH3:11])[CH:2]=2)[CH:17]([C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([O:13][CH3:12])[CH:15]=2)[NH:10][C:8]1=[O:9])([CH3:27])[CH3:23]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6142N-(3-Methylphenyl)ureaHCID 6395Methanesulfonic AcidHCID 115693-Methoxybenzaldehyde

Product 1

HCID 203719553,4-dihydro-1-isopropyl-4-(3-methoxyphenyl)-7-methyl-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
110 °C

Procedure

To a vessel equipped with agitation means, thermometer and a reflux condenser is added 6.40 g of N-isopropyl, N-(m-tolyl) urea, 22.21 g of m-methoxy benzaldehyde, and 255 ml of toluene. The temperature of the mixture is slowly raised (about 25 min.) to 110° C to start refluxing. After refluxing for 5 min. the temperature is lowered to 100° C and 0.12 g (0.082 ml) of methanesulphonic acid is added. The temperature is again increased to 110° C and refluxing maintained for 3 hours. The reaction mixture is then allowed to cool to room temperature, washed 4 times with dilute sulfuric acid (20% w/v) resulting in the formation of a brown-orange gummy material (undesirable material). The organic phase is then washed 4 times with 25 ml portion of water (pH of last wash 5), then dried over anh. soidum sulfate and evaporated (steam distilled) to obtain a residue. The residue is taken up in benzene, and chromatographed on a silica column; starting with benzene then increasing proportions of chloroform (20%, 50%, then 100% chloroform). The samples obtained from 100% chloroform are combined, evaporated to dryness, then crystallized from chloroform to obtain 3,4-dihydro-1-isopropyl-4-(3--methoxyphenyl)-7-methyl-2(1H)-Quinazolinone, mp 167-169.

Workup

  1. customTo a vessel equipped with agitation means
  2. temperatureto start refluxing
  3. temperatureAfter refluxing for 5 min. the temperature
  4. customis lowered to 100° C
  5. temperatureThe temperature is again increased to 110° C
  6. temperaturerefluxing
  7. temperaturemaintained for 3 hours
  8. temperatureto cool to room temperature
  9. washwashed 4 times with dilute sulfuric acid (20% w/v)
  10. customresulting in the formation of a brown-orange gummy material (undesirable material)
  11. washThe organic phase is then washed 4 times with 25 ml portion of water (pH of last wash 5)
  12. dry with materialdried over anh. soidum sulfate
  13. customevaporated
  14. distillation(steam distilled)
  15. customto obtain a residue
  16. customchromatographed on a silica column
  17. customThe samples obtained from 100% chloroform
  18. customevaporated to dryness
  19. customcrystallized from chloroform

Sources & evidence

ORD record
ord-c2bbf5e83fc5427d9c63ae9bee786b82
Source dataset
uspto-grants-1978_01
Patent number
US04071516

Reaction notes

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