Trityl chloride → HCID 22915640, compound

HRID 1377968Notes

Reaction equation

HRID 1377968 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 10 N 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 mls 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-e204673f90424b41a049e40eaead717b
Source dataset
uspto-grants-1997_09
Patent number
US05665881

Reaction notes

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