1-(2-Hydroxyethyl)-5,6-dimethylbenzimidazole → 2-(5,6-Dimethylbenzimidazolyl)ethylphosphoric acid

HRID 1653992Notes

Reaction equation

HRID 1653992 reaction equation
OCC[N:4]1[C:8]2[CH:9]=[C:10]([CH3:14])[C:11]([CH3:13])=[CH:12][C:7]=2[N:6]=[CH:5]1.[NH+]1C=CC=CC=1.C([CH2:23][CH2:24][O:25][P:26](=[O:29])([O-:28])[O-:27])#N.[NH+]1C=CC=CC=1>N1C=CC=CC=1.O>[CH3:14][C:10]1[C:11]([CH3:13])=[CH:12][C:7]2[N:6]=[C:5]([CH2:23][CH2:24][O:25][P:26](=[O:27])([OH:29])[OH:28])[NH:4][C:8]=2[CH:9]=1

Participants

5

Reactant 2

HCID 200789561-(2-Hydroxyethyl)-5,6-dimethylbenzimidazoleHCID 69780213Pyridinium cyanoethylphosphate

Product 1

HCID 200789622-(5,6-Dimethylbenzimidazolyl)ethylphosphoric acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A 0.19 g amount of the crude 1-(2-hydroxyethyl)-5,6-dimethylbenzimidazole and 2 ml of 2-cyanoethylphosphoric acid pyridinium salt solution (1 mmol/ml) were dissolved in 20 ml of dry pyridine, and the solution was concentrated to dryness under a reduced pressure. This process was repeated twice more, and further, the dried material was thoroughly dried by a vacuum pump, dissolved in 20 ml of dry pyridine, 1.67 g of dicyclohexylcarbodiimide was added thereto, and the mixture was stored at room temperature for 2 days. After an addition of water to the product, the mixture was concentrated to dryness under a reduced pressure, followed by an addition of 40 ml of an aqueous LiOH solution (0.5 N) to carry out the reaction at 100° C. for 45 minutes. The reaction mixture was filtered to give a filtrate, which was diluted with water, adjusted to a pH of 2.5 to 3, and then the mixture was applied to an ion exchange column (Dowex 50 (hydrogen ion form)). Elution was effected successively with water and 2 N pyridine, and the fractions eluted with the latter were concentrated to dryness under a reduced pressure to give 0.27 g of crude 2-(5,6-dimethylbenzimidazolyl)ethylphosphoric acid.

Workup

  1. concentrationthe solution was concentrated to dryness under a reduced pressure
  2. customfurther, the dried material was thoroughly dried by a vacuum pump
  3. dissolutiondissolved in 20 ml of dry pyridine
  4. addition1.67 g of dicyclohexylcarbodiimide was added
  5. additionAfter an addition of water to the product
  6. concentrationthe mixture was concentrated to dryness under a reduced pressure
  7. additionfollowed by an addition of 40 ml of an aqueous LiOH solution (0.5 N)
  8. customthe reaction at 100° C. for 45 minutes
  9. filtrationThe reaction mixture was filtered
  10. customto give a filtrate, which
  11. washElution
  12. washthe fractions eluted with the
  13. concentrationlatter were concentrated to dryness under a reduced pressure

Sources & evidence

ORD record
ord-4ecba39144984ea1986c41c5e19e7a0b
Source dataset
uspto-grants-1995_04
Patent number
US05405839

Reaction notes

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