Trichloroisocyanuric Acid → 2-(2-Cyclopropyl-6-methyl-benzyl)-1H-imidazole

HRID 254554Notes

Reaction equation

HRID 254554 reaction equation
[CH:1]1([C:4]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:5]=2[CH2:6][C:7]2[NH:8][CH2:9][CH2:10][N:11]=2)[CH2:3][CH2:2]1.N12CCCN=C1CCCCC2.ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O>C(#N)C.C(OCC)(=O)C>[CH:1]1([C:4]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:5]=2[CH2:6][C:7]2[NH:11][CH:10]=[CH:9][N:8]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 6909Trichloroisocyanuric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 589518352-(2-cyclopropyl-6-methyl-benzyl)-4,5-dihydro-1H-imidazole

Product 1

HCID 589517612-(2-Cyclopropyl-6-methyl-benzyl)-1H-imidazoleYield 16%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared using methodology described in Synlett 2004, 2803-2805. To a solution of 400 mg (1.87 mmol)) 2-(2-cyclopropyl-6-methyl-benzyl)-4,5-dihydro-1H-imidazole in 5 ml acetonitrile at −17° C. were added sequentially 0.50 ml (3.36 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and a solution of 217 mg (0.93 mmol) trichloroisocyanuric acid (TCCA) in 2 ml acetonitrile. The reaction mixture was then stirred for 2 hours at room temperature, before being diluted with ethyl acetate and washed sequentially with water and with saturated brine. The phases were separated and the organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient) to afford 62 mg (16%) of the title compound as a white crystalline solid. MS (ISP): 213.4 ([M+H]+, 100%).

Workup

  1. customThis compound was prepared
  2. washwashed sequentially with water and with saturated brine
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient)

Sources & evidence

ORD record
ord-027b611b5d854a95ad2fe584328a559a
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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