Trityl chloride → HCID 22915640, compound

HRID 2260552Notes

Reaction equation

HRID 2260552 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15])[CH:6]=[CH:5]2.[N-:20]=[N+:21]=[N-:22].[Na+].C([Sn](Cl)(CCCC)CCCC)CCC.[OH-].[Na+].[C:40](Cl)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1(C)C=CC=CC=1.CCCCCC>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]1[N:20]=[N:21][N:22]([C:40]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)([C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)[C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[N:15]=1)[CH:6]=[CH:5]2

Participants

8

Reactant 5

HCID 6456Trityl chlorideHCID 14798Sodium HydroxideHCID 15096Tributyltin ChlorideHCID 33557Sodium AzideHCID 218042392-(6-Methylquinolin-2-yl)benzonitrile

Product 1

HCID 22915640HCID 22915640, compoundYield 377.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Procedure

3.5 ml of toluene were added to 855 mg (3.5 mmol) of 2-(6-methyl-quinolin-2-yl)benzonitrile obtained in Reference Example 8. To the mixture were further added 0.24 g (0.68 mmol) of sodium azide and 1 ml (3.83 mmol) of tributyltin chloride. After heating under reflux for 45 hours, the mixture was allowed to cool and diluted with 7 ml of toluene. To the mixture were added 0.4 ml (4 mmol) of a 10N sodium hydroxide aqueous solution and 1.01 g (3.61 mmol) of tritylchloride with stirring. After stirring at room temperature for 1.5 hours, 15 ml of hexane were added to the mixture and the solid material was collected by filtration. The thus obtained solid material was washed with 10 ml of water twice and then 5 ml of methanol three times. The filter cake was dried under vacuum to obtain 1.36 g of 5-[2-(6-methylquinolin-2-yl)phenyl] -2-triphenylmethyl-2H-tetrazole.

Workup

  1. customobtained in Reference Example 8
  2. temperatureAfter heating
  3. temperatureunder reflux for 45 hours
  4. temperatureto cool
  5. stirringAfter stirring at room temperature for 1.5 hours
  6. filtrationthe solid material was collected by filtration
  7. washThe thus obtained solid material was washed with 10 ml of water twice
  8. customThe filter cake was dried under vacuum

Sources & evidence

ORD record
ord-590f50a7dc1b4dcd936a11fc03322612
Source dataset
uspto-grants-1995_12
Patent number
US05478832

Reaction notes

Loading…