Cyclohexene → HCID 178526908, compound

HRID 653112Notes

Reaction equation

HRID 653112 reaction equation
Br[C:2]1[O:3][C:4]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]3[NH:22][N:21]=[N:20][N:19]=3)=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1CCCCC=1.[N+:29]([O-:34])([N+]([O-])=O)=[O:30]>C(O)(=O)C>[N+:29]([C:2]1[O:3][C:4]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]3[NH:22][N:21]=[N:20][N:19]=3)=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([O-:34])=[O:30]

Participants

5

Reactant 3

HCID 8079CyclohexeneHCID 25352Nitrogen oxide (N2O4)HCID 178419493HCID 178419493, compound

Product 1

HCID 178526908HCID 178526908, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 1.9 g. (0.005 mole) of 2-bromo-3-phenyl-5-tetrazolylmethylbenzofuran in 50 ml. of warm acetic acid and 1 ml. of cyclohexene is added 1 g. of dinitrogen tetraoxide. The mixture is heated on a steam bath for 30 minutes, then cooled to ice bath temperature. The product is separated by filtration, washed with acetic acid and diethyl ether and recrystallized from ethanol to provide yellow needles of 2-nitro-3-phenyl-5(1H-tetrazol-5-ylmethyl)benzofuran, m.p. 245°-247° C. having the structure

Workup

  1. temperatureThe mixture is heated on a steam bath for 30 minutes
  2. temperaturecooled to ice bath temperature
  3. customThe product is separated by filtration
  4. washwashed with acetic acid and diethyl ether
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-99f4da955f5f4e5e85cf2b9a823b7f13
Source dataset
uspto-grants-1987_06
Patent number
US04675320

Reaction notes

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