Acetic Acid → HCID 22493750, compound

HRID 1643183Notes

Reaction equation

HRID 1643183 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 (1g) in acetic acid (10 mL) and 40% aqueous formaldehyde (2 mL) is refluxed for 14 hours. 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).

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-627afb90a37749b4835f7080452eeff5
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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