Methanol → HCID 21449083, compound

HRID 596884Notes

Reaction equation

HRID 596884 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:12]2[O:16][C:15]([C:17](=[NH:21])OCC)=[CH:14][CH:13]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].CO[CH:24](OC)[CH2:25][NH2:26].CO>Cl>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:12]2[O:16][C:15]([C:17]3[NH:21][CH:24]=[CH:25][N:26]=3)=[CH:14][CH:13]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 89728Aminoacetaldehyde dimethyl acetalHCID 21437378HCID 21437378, compound

Product 1

HCID 21449083HCID 21449083, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 52.0 g (0.167 mole) of ethyl 5-(3,4-dimethoxyphenyl)-2-furimidate hydrochloride, 19.3 g (0.184 mole) of aminoacetaldehyde dimethyl acetal and 800 ml of anhydrous methanol was heated to reflux with dissolution. The solution was refluxed for 5 hours and the solvent was then removed on the Calab evaporator yielding a residual oil which was stirred in 800 ml of 3N HCl for ca. 20 hours at a temperature of 70°. The resulting solid was washed in refluxing acetic acid, filtered hot and dried at 100° to yield 14.5 g (28%) of 2-[5-(3,4-dimethoxyphenyl)-2-furyl]imidazole hydrochloride. An analytical sample was prepared by washing a sample a second time in refluxing acetic acid and drying in the vacuum piston at the temperature of refluxing water, m.p. 288°-289°.

Workup

  1. temperaturewas heated
  2. temperatureto reflux with dissolution
  3. temperatureThe solution was refluxed for 5 hours
  4. customthe solvent was then removed on the Calab evaporator
  5. customyielding a residual oil which
  6. washThe resulting solid was washed
  7. temperaturein refluxing acetic acid
  8. filtrationfiltered hot
  9. customdried at 100°

Sources & evidence

ORD record
ord-d5a5865faeaf47f9bf3ed774ecd0ad14
Source dataset
uspto-grants-1977_03
Patent number
US04012415

Reaction notes

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