Water → HCID 18173786, compound

HRID 2399880Notes

Reaction equation

HRID 2399880 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[N-:14]=[N+:15]=[N-:16].[Li+].O>CN(C=O)C>[N:14]([CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 962WaterHCID 88163Lithium azideHCID 27645871-(2-Chloroethoxy)-4-nitrobenzene

Product 1

HCID 18173786HCID 18173786, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.12 g (5.55 mmol) of 4-nitro 2-chloroethyl ether (Example 212) and lithium azide (544 mg, 11.1 mmol) in 3 mL of DMF was heated at 60° C. in an oil bath overnight under nitrogen atmosphere. The reaction was poured into water and extracted with ethyl acetate. The organics were washed with water and brine and dried over anhydrous magnesium sulfate and concentrated to give 1.12 g (97%) of the product: 1H NMR (200 MHz, CDCl3) δ8.18 (d, 2H, J=9Hz), 6.96 (d, 2H, J=9Hz), 4.21 (t, 2H, J=5Hz), 3.63 (t, 2H, J=5Hz).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organics were washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e21c0ad2a5874e68ba920e261cbc5836
Source dataset
uspto-grants-1995_09
Patent number
US05451677

Reaction notes

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