Phosphoric Acid → HCID 69134419, compound

HRID 969507Notes

Reaction equation

HRID 969507 reaction equation
P(=O)(O)(O)O.[CH3:6][N:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:17][CH:18]=[CH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:15]([OH:16])[C:10]=2[N:9]=[C:8]1[CH3:26].[OH-].[Na+]>O>[CH3:26][C:8]1[N:7]([CH3:6])[C:11]2[CH:12]=[CH:13][C:14]3[CH2:17][CH2:18][CH:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[O:16][C:15]=3[C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 69134432HCID 69134432, compound

Product 1

HCID 69134419HCID 69134419, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 5 ml phosphoric acid (85%) and 260 mg (0.9 mmol) 1,2-dimethyl-5-(3phenyl-allyl)-1H-benzimidazol-4-ol was heated at 90° C. for 90 min. After cooling to room temperature, the reaction mixture was poured into water (400 ml), neutralized with 6N sodium hydroxide solution and extracted with dichloromethane (4×300 ml). The organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (toluene/dioxane=2:1) to afford 24.5 mg (10%) of the title compound as a white solid. m. p. 161°-164° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with dichloromethane (4×300 ml)
  3. dry with materialThe organic layers were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (toluene/dioxane=2:1)

Sources & evidence

ORD record
ord-23967b533a3d49e2be2703949ea74070
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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