Hydrochloric Acid → 5-(2-Bromophenyl)-1H-tetrazole

HRID 373619Notes

Reaction equation

HRID 373619 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[N-:10]=[N+:11]=[N-:12].[Na+].C([Sn](Cl)(CCCC)CCCC)CCC.Cl>C1(C)C(C)=CC=CC=1.O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]1[NH:12][N:11]=[N:10][N:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 15096Tributyltin ChlorideHCID 162722-BromobenzonitrileHCID 33557Sodium Azide

Product 1

HCID 1784193735-(2-Bromophenyl)-1H-tetrazoleYield 76%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 64 g (350 mmol) sample of 2-bromobenzonitrile (Aldrich) was dissolved in 650 mL of xylene and treated with 22.75 g (350 mmol) of sodium azide and 95 mL (350 mmol) of tributyltin chloride at reflux for 48 h. The reaction was filtered; the filtrate was treated with 50 mL of anhydrous tetrahydrofuran (THF) and 20 g (550 mmol) of hydrogen chloride. The reaction was stirred for 2 h; filtration gave 59.6 g (76%) of 5-(2-bromophenyl)-1H-tetrazole: mp 178-180° C.; NMR (DMSO-d6) δ 7.50-7.64 (m, 2H), 7.67-7.74 (m, 1H), 7.83-7.91 (m, 1H). A 41.8 g (187 mmol) sample of this material was dissolved in 650 mL of methylene chloride and treated with 55.5 g (193 mmol) of triphenylmethyl chloride and 30 mL (220 mmol) of anhydrous triethylamine. The reaction was stirred overnight at reflux, cooled to ambient temperature, washed with water,

Workup

  1. temperatureat reflux for 48 h
  2. filtrationThe reaction was filtered
  3. filtrationfiltration

Sources & evidence

ORD record
ord-17fc21c95b2244369c743ae3ea210cd4
Source dataset
uspto-grants-1992_11
Patent number
US05164403

Reaction notes

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