Methanol → HCID 59864849, compound

HRID 2423299Notes

Reaction equation

HRID 2423299 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:22][C:23]([OH:25])=[O:24])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:18]=[CH:17][C:12]2[NH:13][C:14]([CH3:16])=[N:15][C:11]=2[C:10]=1[N+:19]([O-:21])=[O:20].[CH3:26]O>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:18]=[CH:17][C:12]2[NH:13][C:14]([CH3:16])=[N:15][C:11]=2[C:10]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 887MethanolHCID 59864777HCID 59864777, compound

Product 1

HCID 59864849HCID 59864849, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Under an N2 atmosphere, 2-(3-chloro-4-(2-methyl-4-nitro-1H-benzo[d]imidazol-5-yloxy)phenyl)acetic acid (0.331 0.915 mmol) was dissolved in methanol and concentrated sulfuric acid (3 drops) was added. The reaction was heated to reflux for 2.5 h, cooled to room temperature and concentrated in vacuo. The residue was partitioned between saturated NaHCO3 (aq) and ethyl acetate. The layers were separated and the aqueous layer washed with additional ethyl acetate (2×). The organics were combined, dried (Na2SO4), and concentrated in vacuo. Flash column chromatography of the residue, eluting 0% to 3% methanol in dichloromethane, afforded title compound. LC-MS ESI (pos.) m/z: 376.0 (M+H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2.5 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between saturated NaHCO3 (aq) and ethyl acetate
  5. customThe layers were separated
  6. washthe aqueous layer washed with additional ethyl acetate (2×)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. washFlash column chromatography of the residue, eluting 0% to 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-2d55826d30914727bc4f7f4ee1547e9b
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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