Acetic Acid → 1-(3-Benzylamino-phenyl)-imidazolidin-2-one

HRID 386471Notes

Reaction equation

HRID 386471 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH2:11][NH:10][C:9]2=[O:13])[CH:5]=[CH:6][CH:7]=1.[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C.[BH4-].[Na+]>O1CCCC1>[CH2:14]([NH:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH2:11][NH:10][C:9]2=[O:13])[CH:5]=[CH:6][CH:7]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 246884361-(3-Aminophenyl)imidazolidin-2-one

Product 1

HCID 436966011-(3-Benzylamino-phenyl)-imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(3-amino-phenyl)-imidazolidin-2-one (0.27 g, 1.5 mmol), benzaldehyde (0.17 ml, 1.7 mmol) and acetic acid (0.13 ml, 2.2 mmol) in dry tetrahydrofuran (10 ml) was stirred at room temperature for 6 hrs. Sodium borohydride (0.14 g, 3.8 mmol) was added and the reaction stirred at room temperature overnight. The reaction mixture was quenched with water (25 ml) then extracted with dichloromethane (3×50 ml). The organic extracts were combined, dried (magnesium sulphate) and concentrated in vacuo. HPLC retention time 7 min. Mass spectrum (ES+) m/z 268 (M+H).

Workup

  1. customThe reaction mixture was quenched with water (25 ml)
  2. extractionthen extracted with dichloromethane (3×50 ml)
  3. dry with materialdried (magnesium sulphate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4943935fc031483a8293761104aedbec
Source dataset
uspto-grants-2013_02
Patent number
US08372840B2

Reaction notes

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