Sodium Azide → 1-(Azidomethyl)-4-methoxybenzene

HRID 1480402Notes

Reaction equation

HRID 1480402 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+]>CN(C=O)C.CCOCC>[N:11]([CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[N+:12]=[N-:13]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 109317671-(Azidomethyl)-4-methoxybenzene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To 4-methoxybenzyl chloride (8.52 mL, 62.8 mmol) in DMF (40 ml) was added sodium azide (4.08 g, 62.8 mmol). The suspension formed was stirred at RT for 24 hrs. The reaction mixture was diluted with ether (400 ml) and washed with water (2×200 mL) and brine (20 ml). The organic layers were dried (MgSO4) and concentrated (water bath temp 20° C.) under reduced pressure to afford the title compound;

Workup

  1. customThe suspension formed
  2. washwashed with water (2×200 mL) and brine (20 ml)
  3. dry with materialThe organic layers were dried (MgSO4)
  4. concentrationconcentrated (water bath temp 20° C.) under reduced pressure

Sources & evidence

ORD record
ord-77ea889114404742a17115dc1bb73c05
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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