Ammonia → 2-hydroxymethyl-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid methyl ester

HRID 896371Notes

Reaction equation

HRID 896371 reaction equation
[OH:1][CH2:2][C:3]1[N:7]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[C:6]2[CH:13]=[CH:14][C:15]([C:17]([OH:19])=[O:18])=[CH:16][C:5]=2[N:4]=1.S(=O)(=O)(O)O.N.O.[CH3:27]O>>[CH3:27][O:18][C:17]([C:15]1[CH:14]=[CH:13][C:6]2[N:7]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[C:3]([CH2:2][OH:1])=[N:4][C:5]=2[CH:16]=1)=[O:19]

Participants

6

Reactant 5

HCID 222AmmoniaHCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 223493222-hydroxymethyl-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid

Product 1

HCID 697080682-hydroxymethyl-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid methyl esterYield 96%

Procedure

A mixture of 2-hydroxymethyl-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid (2.4 g, 9.1 mmol) and concentrated sulfuric acid (1.1 g, 10.9 mmol) in methanol (30 mL) was heated at reflux for 40 hrs. The solution was cooled to room temperature, the pH adjusted to 8-9 with concentrated ammonia, and water was added. A white precipitate formed that was collected by filtration and washed with water. The product was dried in vacuo to yield 2-hydroxymethyl-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid methyl ester (2.4 g, 96%) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 40 hrs
  3. additionwas added
  4. customA white precipitate formed
  5. filtrationthat was collected by filtration
  6. washwashed with water
  7. customThe product was dried in vacuo

Sources & evidence

ORD record
ord-d2227692765b4c1d9c355d24a4b97e0a
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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