18-Crown-6 → HCID 59864777, compound

HRID 2423298Notes

Reaction equation

HRID 2423298 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7]([CH3:9])=[N:8][C:4]=2[C:3]=1[N+:12]([O-:14])=[O:13].[F-].[K+].[Cl:17][C:18]1[CH:19]=[C:20]([CH2:25][C:26]([OH:28])=[O:27])[CH:21]=[CH:22][C:23]=1[OH:24].C1OCCOCCOCCOCCOCCOC1>CS(C)=O.O.Cl>[Cl:17][C:18]1[CH:19]=[C:20]([CH2:25][C:26]([OH:28])=[O:27])[CH:21]=[CH:22][C:23]=1[O:24][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7]([CH3:9])=[N:8][C:4]=2[C:3]=1[N+:12]([O-:14])=[O:13]

Participants

8

Reactant 4

HCID 2855718-Crown-6HCID 1185343-Chloro-4-hydroxyphenylacetic acidHCID 522689Potassium FluorideHCID 54016193HCID 54016193, compound

Product 1

HCID 59864777HCID 59864777, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Under an N2 atmosphere, 5-fluoro-2-methyl-4-nitro-1H-benzo[d]imidazole (0.233 g, 1.19 mmol) was treated with Al2O3 supported potassium fluoride (0.583 g, 40 wt. %), 3-chloro-4-hydroxyphenylacetic acid (0.223 g, 1.19 mmol) and 18-crown-6 (0.031 g, 0.119 mmol) in DMSO (1 mL). The reaction was heated 80° C. for 20 h. Upon cooling to room temperature, the reaction was diluted with water and 1N HCl was added to pH 5. The reaction was extracted with ethyl acetate (3×). The organics were combined, dried (Na2SO4), filtered and concentrated in vacuo. Flash column chromatography of the residue, eluting with 0% to 10% methanol in dichloromethane, afforded the title compound. LC-MS ESI (pos.) m/z: 362.0 (M+H).

Workup

  1. temperatureUpon cooling to room temperature
  2. additionwas added to pH 5
  3. extractionThe reaction was extracted with ethyl acetate (3×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washFlash column chromatography of the residue, eluting with 0% to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-32b65dc3e2bc47448eac34015075a93a
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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