Benzo-1,3-dioxole-5-methylamine → HCID 18796703, compound

HRID 1938516Notes

Reaction equation

HRID 1938516 reaction equation
[CH2:1]([NH2:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.[CH3:12][O:13][C:14]1[N:23]=[C:22](OC)[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:26][CH3:27])[CH:20]=2)[N:15]=1>CS(C)=O>[CH3:12][O:13][C:14]1[N:23]=[C:22]([NH:11][CH2:1][C:2]2[CH:10]=[CH:9][C:8]3[O:7][CH2:6][O:5][C:4]=3[CH:3]=2)[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:26][CH3:27])[CH:20]=2)[N:15]=1

Participants

4

Reactant 2

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 18796677HCID 18796677, compound

Product 1

HCID 18796703HCID 18796703, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3.75 g (24.8 mmol) of piperonylamine was added to a solution of 2.00 g (8.26 mmol) of the 2,4,6-trimethoxyquinazoline prepared in Example 88 in dimethyl sulfoxide (15 ml). The obtained mixture was stirred under heating at 150° to 160° C. After one hour, the reaction mixture was purified by silica gel column chromatography (ethyl acetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give 0.50 g of the title compound as a pale-yellow crystal. molecular formula; C18H17 N3O4

Workup

  1. temperatureunder heating at 150° to 160° C
  2. customthe reaction mixture was purified by silica gel column chromatography (ethyl acetate/n-hexane)
  3. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-8a397e13dbba4b89a6dfb107163b7786
Source dataset
uspto-grants-1997_12
Patent number
US05693652

Reaction notes

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