Trityl chloride → (N-triphenylmethyltetrazol-5-yl]thiophene

HRID 1614674Notes

Reaction equation

HRID 1614674 reaction equation
[C:1]([C:3]1[S:4][CH:5]=[CH:6][CH:7]=1)#[N:2].[Sn]([N:12]=[N+:13]=[N-:14])(C)(C)C.[C:15](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCN(CC)CC>C1(C)C=CC=CC=1.C(Cl)Cl.CCOCC.CCOC(C)=O>[C:16]1([C:15]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:12]2[C:1]([C:3]3[S:4][CH:5]=[CH:6][CH:7]=3)=[N:2][N:14]=[N:13]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 660872-ThiophenecarbonitrileHCID 5104973Azido(trimethyl)stannane

Product 1

HCID 16637535(N-triphenylmethyltetrazol-5-yl]thiopheneYield 80%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

To a solution of 2-cyanothiophene (1.4 g; 12.8 mmol) in dry toluene (10 ml) was added Me3SnN3 (2.8 g; 13.65 mmol). The mixture was stirred at reflux under N2 for 12 hours. The reaction was cooled to room temperature diluted with CH2Cl2 and washed with 2N HCl soln and H2O. The organic was dried over anhydrous MgSO4 and concentrated in vacuo. The residue, containing the free tetrazole, was dissolved in CH2Cl2 (10 mL) and Ph3CCl (3.2 g; 0.9 equiv.) and NEt3 (3.6 mL) were added. After 20 minutes the mixture was diluted with Et2O/EtOAc and washed with 1N NaOH, 10% citric acid and brine. The organic was dried over anhydrous MgSO4 and concentrated in vacuo. The product was purified by recrystallization from hexanes. The titled compound was isolated in 80% yield, Rf=0.33 (10:1 hex/EtOAc).

Workup

  1. temperatureat reflux under N2 for 12 hours
  2. washwashed with 2N HCl soln and H2O
  3. dry with materialThe organic was dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. additionThe residue, containing the free tetrazole
  6. dissolutionwas dissolved in CH2Cl2 (10 mL)
  7. washwashed with 1N NaOH, 10% citric acid and brine
  8. dry with materialThe organic was dried over anhydrous MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe product was purified by recrystallization from hexanes

Sources & evidence

ORD record
ord-648b3253caf943caa4c7c20276bb9a82
Source dataset
uspto-grants-1993_03
Patent number
US05198438

Reaction notes

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