Trityl chloride → 2-Trityl-5-methyl tetrazole

HRID 1746433Notes

Reaction equation

HRID 1746433 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[N:4][N:3]=1.[OH-].[Na+].Cl[C:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH3:1][C:2]1[N:3]=[N:4][N:5]([C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:6]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 14798Sodium HydroxideHCID 178434708HCID 178434708, compound

Product 1

HCID 109583602-Trityl-5-methyl tetrazoleYield 37.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 5-methyl-1H-tetrazole (1.513 g, 18.00 mmol), tetrabutylammonium bromide (0.029 g, 0.090 mmol) and sodium hydroxide (18.90 mL, 18.90 mmol) in dichloromethane (DCM) (25 mL) stirred under nitrogen at room temperature, was added (chloromethanetriyl)tribenzene (5.02 g, 18 mmol). The reaction mixture was stirred at 20° C. for 72 hours. The reaction was quenched with water, then partitioned between dichloromethane (10 mL) and water (25 mL). The organic phase was separated (hydrophobic frit) and the aqueous phase re-extracted (stirred for 5 min) with additional DCM (10 mL), then separated with a hydrophobic frit. The combined organic fractions were washed with water (2×25 mL), 5% aqueous sodium bicarbonate (10 mL) and brine (10 mL). The organic phase was evaporated in vacuo to give a white solid. Recrystallisation from hot ethyl acetate (8 mL/g) provided the product as a white solid (2.2 g). LCMS RT 1.35 mins.

Workup

  1. customThe reaction was quenched with water
  2. custompartitioned between dichloromethane (10 mL) and water (25 mL)
  3. customThe organic phase was separated (hydrophobic frit)
  4. extractionthe aqueous phase re-extracted
  5. stirring(stirred for 5 min) with additional DCM (10 mL)
  6. customseparated with a hydrophobic frit
  7. washThe combined organic fractions were washed with water (2×25 mL), 5% aqueous sodium bicarbonate (10 mL) and brine (10 mL)
  8. customThe organic phase was evaporated in vacuo
  9. customto give a white solid
  10. customRecrystallisation from hot ethyl acetate (8 mL/g)

Sources & evidence

ORD record
ord-37b4dfab85714bbbbe407a163ce2f723
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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