Acetic Acid → HCID 22493750, compound

HRID 1816415Notes

Reaction equation

HRID 1816415 reaction equation
[CH2:1]([N:5]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4].[C:17](O)(=[O:19])C>C=O>[CH2:1]([N:5]1[C:9]([CH2:17][OH:19])=[C:8]([CH3:10])[N:7]=[C:6]1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 22493796HCID 22493796, compound

Product 1

HCID 22493750HCID 22493750, compound

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

A solution of 112 (1 g) in acetic acid (10 mL) and 40% aqueous formaldehyde (2 mL) is refluxed for 14 h. The reaction is then concentrated and dried by repeated reconcentration with toluene. The residue is purified by column chromatography (10% MeOH/CHCl3). The fractions are assayed by GC and those fractions uncontaminated by the isomeric hydroxymethylimidazole combined. Concentration of the combined fractions provides compound 113 (320 mg) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.4-7.6 (m, 6H), 4.61 (s, 2H, CH2OH), 4.02 (t, J=7 Hz, 2H, NCH2), 2.22 (s, 3H, Me), 1.63 (m, 2H), 1.25 (m, 2H), 0.81 (t, J=7 Hz, 3H). Preparation of 1-(1-Butyl)-2-phenyl-4-methyl-5(N-[3,4-methylenedioxyphenyl-]-N-phenylmethyl)aminomethylimidazole

Workup

  1. concentrationThe reaction is then concentrated
  2. customdried
  3. customThe residue is purified by column chromatography (10% MeOH/CHCl3)

Sources & evidence

ORD record
ord-983b9a5c33c44ad99cd0a0be5c2f0249
Source dataset
uspto-grants-2005_04
Patent number
US06884815B1

Reaction notes

Loading…