Sodium hydride → HCID 14349354, compound

HRID 846496Notes

Reaction equation

HRID 846496 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[CH:6][C:5]=1[N:12]1[C:16](=[O:17])[NH:15][N:14]=[N:13]1.I[CH2:19][CH2:20][CH3:21]>CN(C)C=O.O1CCOCCOCCOCCOCCOCC1>[CH2:19]([N:15]1[C:16](=[O:17])[N:12]([C:5]2[CH:6]=[C:7]([Cl:11])[C:8]([Cl:10])=[CH:9][C:4]=2[Cl:3])[N:13]=[N:14]1)[CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 136207173HCID 136207173, compound

Product 1

HCID 14349354HCID 14349354, compoundYield 19.5%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 0.24 g (0.005 mole) of sodium hydride (60% oil suspension) in 45 mL of N,N-dimethylformamide was added 1.3 g (0.005 mole) of 1,4-dihydro-1-(2,4,5-trichlorophenyl)-5H-tetrazol-5-one. The mixture was stirred at room temperature for 15 minutes, then 0.85 g (0.005 mole) of 1-iodopropane and several drops of 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) were added. After complete addition, the reaction mixture was stirred at room temperature for 4 days. The reaction mixture was poured into ice water and the resulting mixture extracted with diethyl ether. The ether extract was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure to leave a solid. The solid was purified by column chromatography on silica gel, eluting with methylene chloride. Recrystallization from ethanol gave 0.3 g of 1,4-dihydro-4-propyl-1-(2,4,5-trichlorophenyl)-5H-tetrazol-5-one as a solid, mp 89°-90° C.

Workup

  1. additionAfter complete addition
  2. stirringthe reaction mixture was stirred at room temperature for 4 days
  3. extractionthe resulting mixture extracted with diethyl ether
  4. extractionThe ether extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated under reduced pressure
  8. customto leave a solid
  9. customThe solid was purified by column chromatography on silica gel
  10. washeluting with methylene chloride
  11. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-59c93a1c9e5b4cfba1a00708fd472454
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

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