Trityl chloride → 5-(2-Bromophenyl)-1-(triphenylmethyl)-1H-tetrazole

HRID 486039Notes

Reaction equation

HRID 486039 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:12][N:11]=[N:10][N:9]=1.[C:13]1([C:19](Cl)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([C:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:11]=[N:10][N:9]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 1784193735-(2-Bromophenyl)-1H-tetrazole

Product 1

HCID 106955555-(2-Bromophenyl)-1-(triphenylmethyl)-1H-tetrazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.50 g of 5-(2-bromophenyl)-1H-tetrazole in 20 ml of CH2Cl2 is added 0.65 g of triphenylmethyl chloride followed by 0.37 ml of triethylamine. The solution is refluxed for 2.5 hours, cooled to room temperature and then washed with water, dried over MgSO4 and concentrated in vacuo. The residue is purified by flash chromatography eluting with ethyl acetate/hexanes (1:5) to provide the desired product.

Workup

  1. temperatureThe solution is refluxed for 2.5 hours
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography
  6. washeluting with ethyl acetate/hexanes (1:5)

Sources & evidence

ORD record
ord-faa3c4f74e64468e90d472a280194d45
Source dataset
uspto-grants-1994_03
Patent number
US05290780

Reaction notes

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