Cyanuric chloride → HCID 22507061, compound

HRID 1368846Notes

Reaction equation

HRID 1368846 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].[N:13]1[C:20]([Cl:21])=[N:19][C:17](Cl)=[N:16][C:14]=1[Cl:15]>O1CCCC1>[Cl:15][C:14]1[N:13]=[C:20]([Cl:21])[N:19]=[C:17]([N:3]2[C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=[C:2]2[CH3:1])[N:16]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 119842-MethylbenzimidazoleHCID 24758Sodium hydride

Product 1

HCID 22507061HCID 22507061, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methylbenzimidazole (5.0 g) was dissolved in tetrahydrofuran (50 ml), and sodium hydride (60% purity, oily) (1.6 g) was added thereto at room temperature. After stirring for 1 hour, cyanuric chloride (7.0 g) was added at room temperature, followed by stirring for 3 hours. Ice water was added, followed by extraction with ethyl acetate, washing with a saturated sodium chloride aqueous solution and drying over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 2.6 g of the desired product as a white powder (m.p. at least 300° C.).

Workup

  1. customat room temperature
  2. stirringby stirring for 3 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washwashing with a saturated sodium chloride aqueous solution
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1d2a50c2c02e431f8bc9e3e3e6c8978a
Source dataset
uspto-grants-2003_06
Patent number
US06576631B1

Reaction notes

Loading…