Sodium Azide → 2-(Azidomethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinone

HRID 1252604Notes

Reaction equation

HRID 1252604 reaction equation
Cl[CH2:2][C:3]1[N:4]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1.[N-:25]=[N+:26]=[N-:27].[Na+]>C(#N)C.C1OCCOCCOCCOCCOCCOC1>[N:25]([CH2:2][C:3]1[N:4]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1)=[N+:26]=[N-:27]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 141824862-(chloromethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinone

Product 1

HCID 141824732-(Azidomethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinoneYield 89.5%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2.0 g (6 mmol) of 2-(chloromethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinone in 20 ml of acetonitrile was added 3.9 g (60 mmol) of sodium azide and 0.1 g of 18-crown-6, and the mixture was heated to reflux for four hours. The salts were filtered off by suction, and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate-methanol 8:2) yielding 1.86 g of the title compound, melting point 120° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for four hours
  3. filtrationThe salts were filtered off by suction
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate-methanol 8:2)

Sources & evidence

ORD record
ord-a24bdac3fd3644b5bc349cda0718157b
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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