Hydrochloric Acid → HCID 22058584, compound

HRID 1828821Notes

Reaction equation

HRID 1828821 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH3:23])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][C:11]=2[Cl:22])[C:6]=1[CH:7]=[O:8].CC(=CC)C.P([O-])(O)(O)=[O:30].[Na+].Cl([O-])=O.[Na+].Cl>C(O)(C)(C)C.O>[Cl:1][C:2]1[N:3]=[C:4]([CH3:23])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][C:11]=2[Cl:22])[C:6]=1[C:7]([OH:30])=[O:8]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 22058630HCID 22058630, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 22058584HCID 22058584, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

4-Chloro-1-(2-chloro-4-(1-pentyloxy)benzyl)-2-methyl-1H-imidazole-5-carbaldehyde (400 mg) was dissolved in t-butanol (8 ml), and 2-methyl-2-butene (355 mg) and aqueous sodium dihydrogenphosphate (135 mg) solution (2 ml) were added. To this reaction mixture was added sodium chlorite (356 mg) over 2 min and the mixture was stirred at room temperature for 24 hr. 1N Hydrochloric acid was added under ice-cooling to adjust to pH 4. Water (20 ml) was added and the precipitated crystals were collected by filtration. The crystals were dried by heating under reduced pressure to give 4-chloro-1-(2-chloro-4-(1-pentyloxy)benzyl)-2-methyl-1H-imidazole-5-carboxylic acid (387 mg) as colorless crystals.

Workup

  1. temperaturecooling
  2. filtrationthe precipitated crystals were collected by filtration
  3. customThe crystals were dried
  4. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-f774ad464aca4442838db25a4be6b196
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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