HCID 59243456, compound → HCID 20472015, compound

HRID 560080Notes

Reaction equation

HRID 560080 reaction equation
C(O[C:5]([C:18]1[N:19](CC2C=CC=CC=2)[CH:20]=[CH:21][N:22]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=O)C>[Pd].C(O)C>[C:12]1([CH:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:18]2[NH:22][CH:21]=[CH:20][N:19]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 59243456HCID 59243456, compound

Product 1

HCID 20472015HCID 20472015, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A slurry of (1-benzyl-1H-imidazol-2-yl)(diphenyl)methyl acetate (1-3, 13.1 g, 34.0 mmol, 1 equiv) and 10% palladium on carbon (6.03 g, 56.4 mmol, 1.66 equiv) in ethanol (250 mL) was stirred under hydrogen (balloon) for 24 h. The reaction mixture was filtered through a pad of celite and washed thoroughly with ethyl acetate. The combined filtrate was concentrated to dryness, and the residue was suspended in saturated aqueous sodium bicarbonate solution. The product was filtered, washed with water (2×100 mL) followed by a 1:1 mixture of ethyl ether and hexanes (2×50 mL) and air dried to yield 2-(diphenylmethyl)-1H-imidazole (1-4) as a white solid. 1H NMR (300 MHz, DMSO) δ 11.8 (br s, 1H), 7.29 (d, 6H, J=4.3 Hz), 7.21 (m, 4H), 7.03 (br s, 1H), 6.85 (br s, 1H), 5.51 (s, 2H), 1.84 (s, 3H). LRMS m/z (M+H) 235.0 found, 335.1 required.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwashed thoroughly with ethyl acetate
  3. concentrationThe combined filtrate was concentrated to dryness
  4. filtrationThe product was filtered
  5. washwashed with water (2×100 mL)
  6. additionfollowed by a 1:1 mixture of ethyl ether and hexanes (2×50 mL) and air
  7. customdried

Sources & evidence

ORD record
ord-3430ae3f3ceb493c9ca101843e787057
Source dataset
uspto-grants-2011_11
Patent number
US08063090B2

Reaction notes

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