Diethylene Glycol → HCID 59559998, compound

HRID 1177353Notes

Reaction equation

HRID 1177353 reaction equation
C(OC([N:9]1[C:13]2[CH:14]=[C:15]([O:20]C)C=[C:17](C#N)[C:12]=2[N:11]=[C:10]1[CH3:22])(OCC)C)C.[OH-:23].[K+].C(O)[CH2:26][O:27][CH2:28][CH2:29]O>>[CH3:26][O:27][C:28]1[CH:29]=[C:14]([C:15]([OH:20])=[O:23])[C:13]2[N:9]=[C:10]([CH3:22])[NH:11][C:12]=2[CH:17]=1

Participants

4

Reactant 3

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 595600111-(1,1-Diethoxyethyl)-6-methoxy-2-methyl-1H-benzimidazole-4-carbonitrile

Product 1

HCID 59559998HCID 59559998, compound

Conditions

Temperature
150 °C

Procedure

A mixture of 1-(1,1-diethoxy-ethyl)-6-methoxy-2-methyl-1H-benzoimidazole-4-carbonitrile (2.5 g, 8.2 mmol), diethylene glycol (5 mL) and 6 N KOH aqueous solution (2.5 mL) was stirred at 150° C. for 16 hours. The mixture was poured into ice water (15 mL) and washed with ethyl acetate (3×100 mL). The water layer was then adjusted to pH 7-6 with 6 N HCl aqueous solution. The resulting mixture was washed with EtOAc and the water layer was concentrated down to a volume of 10 mL. The crude product was purified by preparative HPLC to obtain 350 mg of dark colored sticky gum product. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.98 (bs, 1H) 7.55 (d, J=2.5 Hz, 1H) 7.51 (d, J=2.5 Hz, 1H) 4.20 (bs, 1H) 3.9 (s, 3H) 2.77 (s, 3H). LRMS for C16H21N3O3 m/z 205 (M−H)−.

Workup

  1. washwashed with ethyl acetate (3×100 mL)
  2. washThe resulting mixture was washed with EtOAc
  3. concentrationthe water layer was concentrated down to a volume of 10 mL
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-cba5441b01f245c5b02ef905701184ee
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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