Benzaldehyde → HCID 13098806, compound

HRID 1884360Notes

Reaction equation

HRID 1884360 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][C:9]2[O:12][CH2:13][O:14][C:8]=2[CH:7]=1)[C:3]([NH2:5])=[O:4].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CS(O)(=O)=O.C1(C)C=CC=CC=1>O>[CH3:1][N:2]1[C:6]2[C:11](=[CH:10][C:9]3[O:12][CH2:13][O:14][C:8]=3[CH:7]=2)[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:5][C:3]1=[O:4]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 1140TolueneHCID 6395Methanesulfonic AcidHCID 13098801HCID 13098801, compound

Product 1

HCID 13098806HCID 13098806, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-methyl-N-[3,4-(methylenedioxy)phenyl]urea (240 mg), benzaldehyde (140 μL) and methanesulfonic acid (50 μL) and toluene (60 mL) was refluxed for 2 h in a flask equipped with a Dean-Stark water separator. After cooling, the solution was washed with water thoroughly, dried over Na2SO4 and concentrated in vacuo. The resulting solid was recrystallized from chloroform/hexane to provided the title compound as a tan solid (70 mg, 20%), mp: 228-230° C. 1H NMR (CDCl3): 7.37-7.30 (m, 5H), 6.53 (s, 1H), 6.28 (s, 1H), 5.91 (d, 1H, J=1.4), 5.89 (d, 1H, J=1.4), 5.46 (s, 1H), 5.11 (br s, 1H), 3.33 (s, 3H). Anal. calcd. for C16H14N2O3: C, 68.08: H, 5.00; N, 9.92. Found: C, 68.06; H, 4.91; N, 9.71.

Workup

  1. temperaturewas refluxed for 2 h in a flask
  2. temperatureAfter cooling
  3. washthe solution was washed with water thoroughly
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid was recrystallized from chloroform/hexane

Sources & evidence

ORD record
ord-e46fa4a695c741cc82a1bdfd99070db7
Source dataset
uspto-grants-2004_07
Patent number
US06765006B2

Reaction notes

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