Benzaldehyde → 1-isopropyl-4-phenyl-6,7-methylenedioxy-3,4-dihydro-2(1H)-quinazolinthione

HRID 1973436Notes

Reaction equation

HRID 1973436 reaction equation
[CH:1]([N:4]([C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[CH:9]=1)[C:5]([NH2:7])=[S:6])([CH3:3])[CH3:2].[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CS(O)(=O)=O.C1(C)C=CC=CC=1>O>[CH:1]([N:4]1[C:8]2[C:13](=[CH:12][C:11]3[O:14][CH2:15][O:16][C:10]=3[CH:9]=2)[CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:7][C:5]1=[S:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 1140TolueneHCID 6395Methanesulfonic AcidHCID 12789468N-isopropyl-N-(3,4-methylenedioxyphenyl)thiourea

Product 1

HCID 127894811-isopropyl-4-phenyl-6,7-methylenedioxy-3,4-dihydro-2(1H)-quinazolinthione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 30 grams of N-isopropyl-N-(3,4-methylenedioxyphenyl)thiourea, 27.6 mls. of benzaldehyde, and 2 mls. of methanesulphonic acid in 500 ml. of toluene is refluxed under a Dean Stark water separator for 4 hours, during which 2 ml. water is collected. The filtered solution is then evaporated to yield a powder. This product is recrystallized from dioxane and water to obtain 1-isopropyl-4-phenyl-6,7-methylenedioxy-3,4-dihydro-2(1H)-quinazolinthione, m.p. 215°-218°C.

Workup

  1. customwater is collected
  2. customThe filtered solution is then evaporated
  3. customto yield a powder
  4. customThis product is recrystallized from dioxane and water

Sources & evidence

ORD record
ord-e010a382348e47a89fb7dc843686dc22
Source dataset
uspto-grants-1976_12
Patent number
US03997564

Reaction notes

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