Hydrochloric Acid → HCID 14062559, compound

HRID 751024Notes

Reaction equation

HRID 751024 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[CH:10][N:9]([O:12]CC(O)=O)[C:8]=2[CH:17]=1)([O-:3])=[O:2].C(OC(=O)C)C.C1COCC1.[ClH:29]>O>[ClH:29].[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[CH:10][N:9]([OH:12])[C:8]=2[CH:17]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 103317062-[(6-Nitro-1H-benzimidazol-1-yl)oxy]acetic acid

Product 1

HCID 14062559HCID 14062559, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(6-Nitro-benzoimidazol-1-yloxy)-acetic acid (6) A mixture of 6-nitro-benzoimidazol-1-yloxy)-acetic acid ethyl ester (5) (250 mg, 0.94 mmol), THF (5 mL), water (1 mL) and concentrated HCl (1 mL) was heated to reflux for 2 hours. The reaction mixture was evaporated and the crude residue was purified by HPLC (21.2×250 mm Phenomenex Luna C18(2) column; flow rate=20 mL/min; linear gradient 0-100% B over 30 minutes; A Buffer=water with 0.1% TFA, B Buffer=acetonitrile with 0.1% TFA). HPLC solvents removed in vacuo to yield yellow solid. Yield 65 mg (29%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customThe reaction mixture was evaporated
  4. customthe crude residue was purified by HPLC (21.2×250 mm Phenomenex Luna C18(2) column
  5. customHPLC solvents removed in vacuo
  6. customto yield yellow solid

Sources & evidence

ORD record
ord-2862ee4ac8784eb09644cc39b42b054c
Source dataset
uspto-grants-2008_07
Patent number
US07405235B2

Reaction notes

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