Methanesulfonic Acid → HCID 18405265, compound

HRID 428616

Reaction equation

HRID 428616 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[CH2:11]([N:18]1[C:22]([CH:23]=[CH:24][C:25](O)=[O:26])=[CH:21][N:20]=[CH:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CS(O)(=O)=O.[OH-].[Na+]>O>[CH2:11]([N:18]1[C:22]([CH:23]2[C:5]3[C:6](=[C:7]([CH3:8])[C:2]([CH3:1])=[C:3]([O:9][CH3:10])[CH:4]=3)[C:25](=[O:26])[CH2:24]2)=[CH:21][N:20]=[CH:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 762692,3-DimethylanisoleHCID 537408633-[1-(Phenylmethyl)-1H-imidazol-5-yl]-2-propenoic acid

Product 1

HCID 18405265HCID 18405265, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
92.5 °C

Procedure

A mixture of 2,3-dimethylanisole (2.0 g), 3-(3-benzyl-3H-imidazol-4-yl)-acrylic acid (3.4 g) and methanesulfonic acid (60 ml) is heated at 90-95° C. for 45 minutes. The cooled reaction mixture is poured into water and is made alkaline with sodium hydroxide solution. The product is extracted into ethyl acetate which is washed with water, dried with sodium sulfate and evaporated in reduced pressure. The crude product is purified by flash chromatography by eluting with methylene chloride-methanol solution. The yield is 1.1 g.

Workup

  1. customThe cooled reaction mixture
  2. extractionThe product is extracted into ethyl acetate which
  3. washis washed with water
  4. dry with materialdried with sodium sulfate
  5. customevaporated in reduced pressure
  6. customThe crude product is purified by flash chromatography
  7. washby eluting with methylene chloride-methanol solution

Sources & evidence

ORD record
ord-089ae1521d8c4576ad26f389f08503fb
Source dataset
uspto-grants-2001_11
Patent number
US06313311B1

Linked notes

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