Hydrochloric Acid → 4-(3-Hydroxy-2-oxo-imidazolidin-1-yl)-butyraldehyde

HRID 251007Notes

Reaction equation

HRID 251007 reaction equation
C[O:2][CH:3](OC)[CH2:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][N:9]([OH:12])[C:8]1=[O:13].Cl.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[OH:12][N:9]1[CH2:10][CH2:11][N:7]([CH2:6][CH2:5][CH2:4][CH:3]=[O:2])[C:8]1=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 672723451-(4,4-Dimethoxy-butyl)-3-hydroxy-imidazolidin-2-one

Product 1

HCID 865947624-(3-Hydroxy-2-oxo-imidazolidin-1-yl)-butyraldehydeYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4,4-Dimethoxy-butyl)-3-hydroxy-imidazolidin-2-one (0.753 g, 3.45 mmol) in THF (3 mL) was added 1.0 N HCl (18 mL) and the mixture was stirred at room temperature overnight. The mixture was saturated with solid Na2CO3 (˜2 g) and extracted with CH2Cl2 (5×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated and provided 0.30 g (51%) of 4-(3-Hydroxy-2-oxo-imidazolidin-1-yl)-butyraldehyde as a yellow oil. 1H NMR (CDCl3) δ 1.83-1.91 (m, 2H), 2.53 (t, 2H, J=6.9 Hz), 3.25 (t, 2H, J=6.9 Hz), 3.30 (t, 2H, J=6.9 Hz), 3.48 (t, 2H, J=6.9 Hz), 7.75 (br s, 1H), 9.70 (s, 1H).

Workup

  1. extractionextracted with CH2Cl2 (5×10 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-97e58fc38fc54085b453813f0349ff48
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

Loading…