Azide → HCID 178514606, compound

HRID 847928Notes

Reaction equation

HRID 847928 reaction equation
Cl.Cl[CH2:3][CH2:4][O:5][CH2:6][C:7]1[N:8]=[CH:9][NH:10][CH:11]=1.[Na].[N-:13]=[N+:14]=[N-:15]>CN(C)C=O>[N:13]([CH2:3][CH2:4][O:5][CH2:6][C:7]1[N:8]=[CH:9][NH:10][CH:11]=1)=[N+:14]=[N-:15]

Participants

5

Reactant 3

HCID 33558AzideHCID 5360545SodiumHCID 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 size 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-azidoethoxymethyl)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 monopiocrate monohydrochloide 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; N, 20.7; Cl, 8.7).

Workup

  1. temperaturewas maintained at 95° for 5 hours
  2. filtrationwith water and filtration
  3. concentrationthe filtrate was 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-08fae15860dd4bf7ae78fc8cf10fc6f7
Source dataset
uspto-grants-1981_10
Patent number
US04293699

Reaction notes

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