Dimethylformamide → 1-(Azidomethyl)-4-methoxybenzene

HRID 1447183Notes

Reaction equation

HRID 1447183 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)C=O>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 6228DimethylformamideHCID 33557Sodium AzideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 109317671-(Azidomethyl)-4-methoxybenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-Methoxybenzyl azide is prepared by stirring a mixture of 35 g. of p-methoxybenzyl chloride and 20 g. of sodium azide in 300 ml. dimethylformamide at room temperature for 30 minutes. The mixture is poured into water and extracted with benzene. The extracts are dried, evaporated to dryness and the residue is vacuum distilled, 34 g., bp 72°-75° C. (0.05 mm) (lit. 118°-118.5° C., 10 mm., reference in example 1).

Workup

  1. additiona mixture of 35 g
  2. extractionextracted with benzene
  3. customThe extracts are dried
  4. customevaporated to dryness
  5. distillationdistilled
  6. custombp 72°-75° C. (0.05 mm) (lit. 118°-118.5° C., 10 mm., reference in example 1)

Sources & evidence

ORD record
ord-9d806a6c4ead4de68a48a54c832a2ff4
Source dataset
uspto-grants-1982_02
Patent number
US04316037

Reaction notes

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