Acetic Anhydride → HCID 59243456, compound

HRID 560079Notes

Reaction equation

HRID 560079 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>N1C=CC=CC=1>[C:27]([O:14][C:13]([C:9]1[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:12]=[CH:11][N:10]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 2852467HCID 2852467, compound

Product 1

HCID 59243456HCID 59243456, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A slurry of (1-benzyl-1H-imidazol-2-yl)(diphenyl)methanol (1-2, 16.0 g, 47.0 mmol, 1 equiv) in acetic anhydride (120 mL) and pyridine (130 mL) was heated at 60° C. for 18 h. The resulting orange slurry was concentrated to dryness. The residue was suspended in saturated aqueous sodium carbonate solution (300 mL) and the resulting precipitate was filtered and washed with water (2×100 mL) followed by ethyl ether (50 mL). The resulting solid was suspended in ethanol, collected by filtration and air dried to afford (1-benzyl-1H-imidazol-2-yl)(diphenyl)methyl acetate (1-3) as white crystals. 1H NMR (300 MHz, CDCl3) δ 7.43 (m, 3H), 7.30 (m, 10H), 7.12 (d, 1H, J=1.2 Hz), 6.86 (m, 2H), 6.77 (d, 1H, J=1.2 Hz), 4.83 (s, 2H), 1.84 (s, 3H). LRMS m/z (M-OAc) 323.1 found, 323.2 required.

Workup

  1. concentrationThe resulting orange slurry was concentrated to dryness
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water (2×100 mL)
  4. filtrationcollected by filtration and air
  5. customdried

Sources & evidence

ORD record
ord-99fd63b7e9724249aa8ebb70c67d0f5a
Source dataset
uspto-grants-2011_11
Patent number
US08063090B2

Reaction notes

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