Ammonia → HCID 22058604, compound

HRID 1828823Notes

Reaction equation

HRID 1828823 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[CH2:7]Cl.[NH3:24].C(=O)([O-])O.[Na+]>C(#N)C>[NH2:24][CH2:7][C:6]1[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:4]([CH3:23])=[N:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 516892Sodium BicarbonateHCID 22058623HCID 22058623, compound

Product 1

HCID 22058604HCID 22058604, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 4-chloro-5-chloromethyl-1-(2-chloro-4-(1-pentyloxy)benzyl)-2-methyl-1H-imidazole (340 mg) in acetonitrile (3 ml) was added gradually to a mixed solvent of 28% aqueous ammonia (6 ml) and acetonitrile (6 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogencarbonate solution was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was applied to silica gel column chromatography and eluted with chloroform/methanol=100/1. The objective fraction was concentrated under reduced pressure to give 5-aminomethyl-4-chloro-1-(2-chloro-4-(1-pentyloxy)benzyl)-2-methyl-1H-imidazole (82 mg) as a pale-brown oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with chloroform/methanol=100/1
  7. concentrationThe objective fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f38439562a5d4d2a92bdd799061661bf
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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