Formaldehyde → 1-(3-chloropropyl)-3-(hydroxymethyl)-1H-benzo[d]imidazol-2(3H)-one

HRID 2362940Notes

Reaction equation

HRID 2362940 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:14].C=O.[C:17]([O-])(=[O:19])C.[Na+]>C(O)(=O)C>[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([CH2:17][OH:19])[C:6]1=[O:14]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 517045Sodium AcetateHCID 18104191-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 580468071-(3-chloropropyl)-3-(hydroxymethyl)-1H-benzo[d]imidazol-2(3H)-oneYield 90.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(3-Chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one (0.30 g, 1.42 mmol), paraformaldehyde (0.0853 g, 2.84 mmol), and sodium acetate (0.117 g, 1.42 mmol) in acetic acid (3 mL) were heated at 65° C. for 20 hours. The mixture was evaporated to dryness, dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate and brine, dried (MgSO4), and evaporated. The residue was purified by PTLC (50% ethyl acetate/hexanes) to give product as a white solid (0.31 g, 90%); NMR (DMSO-d6); 82.06-2.13 (m, 2H); 3.66 (t, J=6.4 Hz, 2H); 3.96 (t, J=6.8 Hz, 2H); 5.22 (d, J=7.2 Hz, 2H); 6.38 (t, J=7.2 Hz, 1H); 7.07 (m, 2H); 7.20-7.22 (m, 1H); 7.23-7.25 (m, 1H); MS for C11H13ClN2O2 m/z 241 (M+H)+.

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by PTLC (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c525e1acbd1d493a8518ff67c8c0dbc4
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

Loading…