Benzyl Chloride → HCID 12752368, compound

HRID 325734Notes

Reaction equation

HRID 325734 reaction equation
[H-].[Na+].[NH:3]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][N:5]=[N:4]1.[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>S1(CCCC1)(=O)=O>[CH2:13]([N:3]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][N:5]=[N:4]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 178470518HCID 178470518, compound

Product 1

HCID 12752368HCID 12752368, compoundYield 117.2%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

A suspension of sodium hydride (0.13 g) in dry sulpholane (10 ml) was treated with ethyl tetrazole-5-carboxylate (0.71 g), and the mixture stirred for 20 minutes at room temperature. Benzyl chloride (0.7 g) was then added, and the mixture was stirred at 60°-65° C. overnight. The mixture was then poured onto ice (25 g) and the resulting oil was separated off and dissolved in diethyl ether (35 ml). The aqueous layer was extracted with a further quantity of diethyl ether (10 ml) and the combined ether extracts were dried over magnesium sulphate. Removal of the ether under reduced pressure gave a mixture (1.36 g) of ethyl 1-benzyl-1H-tetrazole-5-carboxylate and ethyl 2-benzyl-2H-tetrazole-5-carboxylate, containing a little sulpholane.

Workup

  1. stirringthe mixture was stirred at 60°-65° C. overnight
  2. additionThe mixture was then poured onto ice (25 g)
  3. customthe resulting oil was separated off
  4. dissolutiondissolved in diethyl ether (35 ml)
  5. extractionThe aqueous layer was extracted with a further quantity of diethyl ether (10 ml)
  6. dry with materialthe combined ether extracts were dried over magnesium sulphate
  7. customRemoval of the ether under reduced pressure

Sources & evidence

ORD record
ord-b77413ccdd3146c08c9014ba0f294922
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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