Potassium Carbonate → HCID 71620987, compound

HRID 537309Notes

Reaction equation

HRID 537309 reaction equation
[O:1]([CH2:8][C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Cl>CN(C=O)C>[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][N:13]1[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=[C:9]1[CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699943-Methoxybenzyl chlorideHCID 2100742-(Phenoxymethyl)-1H-benzimidazole

Product 1

HCID 71620987HCID 71620987, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A 50 mL flask fitted with a stir-bar and a septum with an Ar inlet was charged with 2-(phenoxymethyl)-1 H-benzimidazole (61) (1.00 g, 4.46 mmol), K2CO3 (1.23 g, 8.92 mmol), and DMF (12 mL). 3-Methoxybenzyl chloride (769 mg, 4.91 mmol) was added, and the suspension was heated in a 100° C. bath for 2 hr. The mixture was cooled, and the solids were filtered off and rinsed with EtOAc (50 mL). The filtrate was then washed with sat'd NH4Cl (2×30 mL), H2O (2×30 mL), and brine (20 mL), filtered through phase separation paper, and concentrated in vacuo to a yellow oil. Upon standing the oil crystallized, and was subsequently collected with hexanes:EtOAc 30:1 (15 mL). Upon drying, 1.41 g of Compound #11 were obtained as an off-white crystalline solid (92%). 1H NMR (300 MHz, CDCl3): δ 7.84 (m, 1H), 7.36-7.25 (m, 5H), 7.21 (t, 1H), 6.82 (dd, 1H), 6.68 (d, 1H), 6.62 (m, 1H), 5.52 (s, 2H), 5.36 (s, 2H), 3.64 (s, 3H) ppm. HPLC analysis (5:10:85 H2O:A1:MeOH) showed a purity of greater than 99% with a retention time of 4.8 min.

Workup

  1. customA 50 mL flask fitted with a stir-bar
  2. temperatureThe mixture was cooled
  3. filtrationthe solids were filtered off
  4. washrinsed with EtOAc (50 mL)
  5. washThe filtrate was then washed with sat'd NH4Cl (2×30 mL), H2O (2×30 mL), and brine (20 mL)
  6. filtrationfiltered through phase separation paper
  7. concentrationconcentrated in vacuo to a yellow oil
  8. customcrystallized
  9. customwas subsequently collected with hexanes:EtOAc 30:1 (15 mL)
  10. customUpon drying

Sources & evidence

ORD record
ord-68cd2a7bdbec40b280db6d24e80afac7
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

Loading…