Methyl iodide → HCID 14031860, compound

HRID 986498Notes

Reaction equation

HRID 986498 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:20]=[C:19]3[N:10]([C:11](=[O:21])[NH:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=43)[N:9]=2)=[CH:4][CH:3]=1.[CH3:22][O-].[Na+].CI>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:20]=[C:19]3[N:10]([C:11](=[O:21])[N:12]([CH3:22])[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=43)[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 135458592104614-80-4

Product 1

HCID 14031860HCID 14031860, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a mixture of 2-(4-chlorophenyl)-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)one (6 g) in dry dimethylsulphoxide (150 ml) is added sodium methoxide (1.3 g). The mixture is heated under nitrogen for one hour at 85° and methyl iodide (1.3 ml) in dimethyl sulphoxide (10 ml) added. A white solid forms rapidly. The reaction mixture is heated three hours longer, cooled and poured into ice water (800 ml). The precipitated white solid is washed with water, air dried (7.2 g) and recrystallized from dimethylacetamide twice to afford pure 2-(4-chlorophenyl)6-methyl-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)one, mp 323°-325°.

Workup

  1. temperatureThe mixture is heated under nitrogen for one hour at 85°
  2. temperatureThe reaction mixture is heated three hours longer
  3. temperaturecooled
  4. washThe precipitated white solid is washed with water, air
  5. customdried (7.2 g)
  6. customrecrystallized from dimethylacetamide twice

Sources & evidence

ORD record
ord-7a4b4f86fa9d4eb0b25da08cc76a5311
Source dataset
uspto-grants-1987_12
Patent number
US04713383

Reaction notes

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