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

HRID 1751016Notes

Reaction equation

HRID 1751016 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); δ2.06-2.13 (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-8485850eda36486497cbf8d2d292a83b
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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