Triethylamine → (3-methoxyphenyl)-(2-methylsulfanyl-4,5-dihydroimidazol-1-yl)methanone

HRID 2223329Notes

Reaction equation

HRID 2223329 reaction equation
I.[CH3:2][S:3][C:4]1[NH:5][CH2:6][CH2:7][N:8]=1.C(N(CC)CC)C.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](Cl)=[O:22]>C(Cl)Cl>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C:21]([N:8]2[CH2:7][CH2:6][N:5]=[C:4]2[S:3][CH3:2])=[O:22])[CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74374m-Anisoyl chlorideHCID 122212281H-Imidazole, 4,5-dihydro-2-(methylthio)-, hydriodide (1:1)

Product 1

HCID 3413160(3-methoxyphenyl)-(2-methylsulfanyl-4,5-dihydroimidazol-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methylsulfanyl-4,5-dihydro-1H-imidazole hydroiodide (1.22 g, 1.0 equiv) in CH2Cl2 (25 mL) under an atmosphere of argon at 0° C. was added triethylamine (1.5 mL, 2.2 equiv) and then 3-methoxybenzoyl chloride (0.78 mL, 1.1 equiv) dropwise. Thereaction mixture was allowed to warm to room temperature and stir for 24 hr. After concentration, the resulting residue was diluted with EtOAc (50 mL) and hexane (50 mL). The mixture was filtered and then the filtrate concentrated and dried under vacuum to give a quantitative yield of (3-methoxyphenyl)-(2-methylsulfanyl-4,5-dihydroimidazol-1-yl)-methanone which was used directly in the next step.

Workup

  1. concentrationAfter concentration
  2. additionthe resulting residue was diluted with EtOAc (50 mL) and hexane (50 mL)
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated
  5. customdried under vacuum

Sources & evidence

ORD record
ord-31cd2216a90643b8bc3a3fbee37cace5
Source dataset
uspto-grants-2008_05
Patent number
US07375125B2

Reaction notes

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