Sodium Hydroxide → HCID 178524846, compound

HRID 1586761Notes

Reaction equation

HRID 1586761 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][C:5]2[C:11]([CH2:12][P:13]([OH:16])([OH:15])=[O:14])=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[O-:17][Mn](=O)(=O)=O.[K+].[OH-].[Na+]>O>[C:2]([C:3]1[NH:4][C:5]2[C:11]([CH2:12][P:13]([OH:16])([OH:15])=[O:14])=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1)([OH:17])=[O:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium Permanganate2×HCID 178527075HCID 178527075, compound

Product 1

HCID 178524846HCID 178524846, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

2-Hydroxymethyl-4-phosphonomethylbenzimidazole (411 mg) and KMnO4 (70 mg) in water (7 mL) containing 3 equivalents of NaOH were warmed to 80° C. KMnO4 (636 mg) was divided into 9 equal portions and added over 3.5 hours. The reaction was stirred at 80° C. for one additional hour then cooled and filtered through diatomaceous earth. The pale yellow solution was concentrated to a yellow solid. The solid was taken up in water and applied to a column of Amberlite CG 400 (0.5×16 cm). The column was eluted with water (50 mL), then 1N HOAc, 2N HOAc, 4N HOAc, and finally 1N HCl (50 mL each). The HCl fractions were pooled and concentrated to a yellow solid. The solid was triturated with water, then collected by suction filtration and washed with a small amount of ethanol and ether to obtain a white solid. H NMR data: D2O (HDO at 4.64 ppm) 3.06 (d, 2H), 7.15 (m, 2H), 7.41 (d, 1H). E.A. Cal'd for C9H9N2O5P.0.6 H2O; C, 40.49, H, 3.85, N, 10.49. Found; C, 40.10, N, 3.57, N, 10.30.

Workup

  1. additionadded over 3.5 hours
  2. temperaturethen cooled
  3. filtrationfiltered through diatomaceous earth
  4. concentrationThe pale yellow solution was concentrated to a yellow solid
  5. washThe column was eluted with water (50 mL)
  6. concentrationconcentrated to a yellow solid
  7. customThe solid was triturated with water
  8. filtrationcollected by suction filtration
  9. washwashed with a small amount of ethanol and ether
  10. customto obtain a white solid

Sources & evidence

ORD record
ord-d9370f9148ca4434b184ce9db1fdc110
Source dataset
uspto-grants-1993_06
Patent number
US05216003

Reaction notes

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