Triethylamine → 2-Acetyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridin-4-yl)methyl-1H-imidazole

HRID 8406Notes

Reaction equation

HRID 8406 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]Cl)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:11]([O:14][CH2:15][C:16]1[N:17]([CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH:18]=[C:19]([CH:21]([CH3:23])[CH3:22])[N:20]=1)(=[O:13])[CH3:12].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(#N)C>[C:11]([O:14][CH2:15][C:16]1[N:17]([CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[C:18]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:19]([CH:21]([CH3:23])[CH3:22])[N:20]=1)(=[O:13])[CH3:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 101305733,5-Dichlorobenzenesulfenyl chlorideHCID 154583312-Acetyloxymethyl-4-isopropyl-1-(pyridin-4-yl)methyl-1H-imidazole

Product 1

HCID 98465722-Acetyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridin-4-yl)methyl-1H-imidazoleYield 82%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of the compound (3) (0.97 g, 4.5 mmol) in toluene (1.88 g) was added dropwise a solution of the compound (10a) (0.87 g, 3.2 mmol) in acetonitrile (4 ml) under ice-cooling for 30 minutes. A solution of triethylamine (0.46 g, 4.5 mmol) in acetonitrile (0.5 ml) was added dropwise thereto for 15 minutes, and the mixture was stirred under ice-cooling for 2 hours. The reaction mixture was concentrated under reduced pressure and extracted with ethyl acetate. The extract was washed with water, concentrated under reduced pressure and purified by column chromatography on silica gel (elution ethyl acetate) to yield the objective (11) (1.17 g) as a crystal. Yield 82%. Mp 133–135° C.

Workup

  1. temperaturecooling for 30 minutes
  2. temperaturecooling for 2 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. concentrationconcentrated under reduced pressure
  7. custompurified by column chromatography on silica gel (elution ethyl acetate)

Sources & evidence

ORD record
ord-1b1cbabccb3541bf91aad69e89164acf
Source dataset
uspto-grants-2006_08
Patent number
US07087764B2

Reaction notes

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