Sodium Hydroxide → HCID 69523045, compound

HRID 969497Notes

Reaction equation

HRID 969497 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]([C:5]1[C:16]([CH2:17][CH2:18][CH:19](O)C2C=CC=CC=2)=[C:15]([OH:27])[C:8]2[N:9]=[C:10]([CH2:13][CH3:14])[N:11]([CH3:12])[C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+]>P(=O)(O)(O)O>[CH3:28][N:2]([CH3:1])[C:3]([C:5]1[C:16]2[CH2:17][CH2:18][CH2:19][O:27][C:15]=2[C:8]2[N:9]=[C:10]([CH2:13][CH3:14])[N:11]([CH3:12])[C:7]=2[C:6]=1[C:5]1[CH:16]=[CH:15][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69135097HCID 69135097, compound

Product 1

HCID 69523045HCID 69523045, compoundYield 113.3%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1.3 g (3.4 mmol) 2-ethyl-7-hydroxy-6-(3-hydroxy-3-phenyl-propyl)-3-methyl-3H-benzoimidazole-5-carboxylic acid dimethylamide in 13 ml 85% orthophosphoric acid was heated to 80° C. After 2 h stirring, the reaction was cooled to room temperature, neutralized with 6M sodium hydroxide (65 ml) and extracted with dichloromethane (4×150 ml). The organic layers were dried over magnesium sulphate and concentrated in vacuo to afford 0.7 g (57%) of the title compound as a white solid. m.p. 195°-197° C.

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. extractionextracted with dichloromethane (4×150 ml)
  3. dry with materialThe organic layers were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc1dbab182244cd6b409a215c598907e
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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