Dimethylformamide → HCID 19001732, compound

HRID 1769994Notes

Reaction equation

HRID 1769994 reaction equation
[CH:1]([CH:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:2].[N-:11]=[N+:12]=[N-:13].[Na+].CN(C)C=O>C(OCC)C>[CH:1]([CH:3]([N:11]=[N+:12]=[N-:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-

Product 1

HCID 19001732HCID 19001732, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 100 grams (655 mmol.) of vinylbenzyl chloride (mixture of m- and p-isomers), 42.6 grams (655 mmol.) of sodium azide and 500 ml. of dimethylformamide was stirred at room temperature for 24 hours. Ethyl ether, 500 ml., was then added and the mixture was extracted with two 300ml. portions of water. The combined aqueous phases were extracted with 500 ml. of ethyl ether, and the combined organic layers were dried over magnesium sulfate, filtered and evaporated to yield 105 grams (100% of theoretical) of vinylbenzyl azide. The structure was confirmed by proton and carbon-13 nuclear magnetic resonance spectroscopy and infrared spectroscopy.

Workup

  1. addition, was then added
  2. extractionthe mixture was extracted with two 300ml
  3. extractionThe combined aqueous phases were extracted with 500 ml
  4. dry with materialof ethyl ether, and the combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ef9056d8ffc3423d9a107b6b206c9d1e
Source dataset
uspto-grants-1995_01
Patent number
US05384361

Reaction notes

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