Potassium Carbonate → 1-Methyl-5-[[7-(3-methyl-5-isoxazolyl)heptyl]thio]-1H-tetrazole

HRID 729101Notes

Reaction equation

HRID 729101 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]Br)[O:4][N:3]=1.[CH3:15][N:16]1[C:20]([SH:21])=[N:19][N:18]=[N:17]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:15][N:16]1[C:20]([S:21][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:5]2[O:4][N:3]=[C:2]([CH3:1])[CH:6]=2)=[N:19][N:18]=[N:17]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133169675-(7-Bromoheptyl)-3-methylisoxazoleHCID 178482017HCID 178482017, compound

Product 1

HCID 540426221-Methyl-5-[[7-(3-methyl-5-isoxazolyl)heptyl]thio]-1H-tetrazoleYield 101.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

7-(3-methylisoxazole-5-yl)heptylbromide (520 mg, 0.002 mol) was added to a mixture of 1-methyltetrazole thiol (232 mg, 0.002 mol) and potassium carbonate (276 mg, 0.002 mol) in anhydrous acetone (20 ml) while stirring.The mixture was heated under reflux for 3 hours. After cooling, the mixturewas filtered and the filtrate was concentrated under reduced pressure. The residual oil as dissolved in dichloromethane (50 ml), washed with water (50 ml×2), with 5% aqueous solution of potassium hydroxide (10 ml) and again with water (50 ml×2). The organic layer was dried over sodium sulfate. Removal of the solvent gave a yellow oil (600 mg) which was purified by elution from a silica gel column using methanol-dichloromethane (5:95) as an eluant to give 80% (472 mg) of a colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. filtrationthe mixturewas filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe residual oil as dissolved in dichloromethane (50 ml)
  7. washwashed with water (50 ml×2), with 5% aqueous solution of potassium hydroxide (10 ml) and again with water (50 ml×2)
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. customRemoval of the solvent

Sources & evidence

ORD record
ord-eca0f73b5545408dbcabcb8f90060d8e
Source dataset
uspto-grants-1991_09
Patent number
US05051515

Reaction notes

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