Methyl Isocyanate → 2-(Methylcarbamoyl)amino-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline

HRID 1900685Notes

Reaction equation

HRID 1900685 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[NH2:5][C:6]1[N:15]=[C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:27])[CH:12]=2)[N:7]=1>CS(C)=O>[CH3:1][NH:2][C:3]([NH:5][C:6]1[N:15]=[C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:27])[CH:12]=2)[N:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 211839282-Amino-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline

Product 1

HCID 211840132-(Methylcarbamoyl)amino-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazolineYield 12.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

4 ml of dimethyl sulfoxide and 260 mg of methyl isocyanate were added to 500 mg of 2-amino-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline. The obtained mixture was stirred at 50° C. for 3 hours and distilled under a reduced pressure to remove excess methyl isocyanate, followed by the addition of chloroform and water. The mixture thus obtained was filtered and the filtrate was extracted with chloroform twice. The organic layers were combined, washed with water twice, dried over magnesium sulfate and distilled under a reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (benzene/acetone) and recrystallized (from benzene/chloroform/ethanol) to give 72 mg of the title compound.

Workup

  1. distillationdistilled under a reduced pressure
  2. customto remove excess methyl isocyanate
  3. additionfollowed by the addition of chloroform and water
  4. customThe mixture thus obtained
  5. filtrationwas filtered
  6. extractionthe filtrate was extracted with chloroform twice
  7. washwashed with water twice
  8. dry with materialdried over magnesium sulfate
  9. distillationdistilled under a reduced pressure
  10. customto remove the solvent
  11. customThe residue was purified by silica gel column chromatography (benzene/acetone)
  12. customrecrystallized (from benzene/chloroform/ethanol)

Sources & evidence

ORD record
ord-a2e048575d4d4591aeb7cd401b3ba80a
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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