Water → 1-(Azidomethyl)-4-methoxybenzene

HRID 325741Notes

Reaction equation

HRID 325741 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[N-:11]=[N+:12]=[N-:13].[Na+].O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:11]=[N+:12]=[N-:13])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 109317671-(Azidomethyl)-4-methoxybenzeneYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of freshly prepared 4-methoxybenzyl chloride (45.85 g) in dry dimethylformamide (150 ml) was treated with sodium azide (19.35 g). The stirred mixture was heated at between 100° and 110° C. for 20 hours, and was then cooled and poured into water (1200 ml). The resulting oil was extracted with diethyl ether (2×500 ml) and the combined ethereal extracts were washed with water (2×250 ml), dried over magnesium sulphate, and evaporated to give crude 4-methoxybenzyl azide (45.3 g).

Workup

  1. temperatureThe stirred mixture was heated at between 100° and 110° C. for 20 hours
  2. temperaturewas then cooled
  3. extractionThe resulting oil was extracted with diethyl ether (2×500 ml)
  4. washthe combined ethereal extracts were washed with water (2×250 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-81045fae251c47d3a466be9181b67633
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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