Sodium Azide → HCID 178514606, compound

HRID 27488Notes

Reaction equation

HRID 27488 reaction equation
Cl.Cl[CH2:3][CH2:4][O:5][CH2:6][C:7]1[N:8]=[CH:9][NH:10][CH:11]=1.[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C)C=O>[N:12]([CH2:3][CH2:4][O:5][CH2:6][C:7]1[N:8]=[CH:9][NH:10][CH:11]=1)=[N+:13]=[N-:14]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 178478571HCID 178478571, compound

Product 1

HCID 178514606HCID 178514606, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred suspension of 4-(2-chloroethoxymethyl)-imidazole hydrochloride (14.7 g.) and sodium azide (9.8 g.) in dry dimethylformamide (103 ml.) was maintained at 95° for 5 hours and then set aside overnight at room temperature. Following dilution with water and filtration the filtrate was concentrated and the residue purified by chromatography on a dry column of alumina using ethanol. The product was basified with potassium carbonate (6.5 g.) in water (3 ml.) and the anhydrous residue was extracted with isopropyl alcohol (3×50 ml.). Concentration of the extracts afforded 4-(2-azidoethoxymethl)imidazole (7.2 g.). Hydrogenation of the azido compound (7.2 g.) in isopropyl alcohol (142 ml.) over platinum oxide catalyst (3.0 g.) gave 4-(2-aminoethoxymethyl)imidazole (6.48 g.). A sample of the monopicrate monohydrochloride had m.p. 139°-140° (from nitromethane). (Found: C, 35.4; H, 3.8; N, 20.5; Cl, 8.8. C12H15ClN6O8 requires: C, 35.4; H, 3.7; l N, 20.7; Cl, 8.7).

Workup

  1. temperaturewas maintained at 95° for 5 hours
  2. filtrationwith water and filtration the filtrate
  3. concentrationwas concentrated
  4. customthe residue purified by chromatography on a dry column of alumina
  5. extractionthe anhydrous residue was extracted with isopropyl alcohol (3×50 ml.)

Sources & evidence

ORD record
ord-ad851abdb3464728bf8d86045080b9b0
Source dataset
uspto-grants-1980_09
Patent number
US04221802

Reaction notes

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