Imidazole → HCID 15388671, compound

HRID 2204134Notes

Reaction equation

HRID 2204134 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8].[NH:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[F:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 97061,2-DifluorobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 15388671HCID 15388671, compoundYield 1.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

1,2-Difluorobenzene (25 mL, 254.0 mmol), imidazole (15.6 g, 228.6 mmol), and potassium carbonate (70.2 g, 508.0 mmol) were suspended in dimethyl sulfoxide (15 mL). The reaction mixture was heated at 110° C. for 72 hours. The reaction mixture was then partitioned between ethyl acetate and was water and washed several times with a saturated aqueous solution of ammonium chloride to remove a small amount of di-imidazole material. The organic layer was then dried over sodium sulfate and evaporated to dryness to yield 1-(2-fluorophenyl)imidazole (430 mg, 1%) that was used without further purification. ESI-MS m/z calc. 162.1, found 163.3 (M+1)+. Retention time 0.26 minutes (3 min run). NMR (400 MHz, DMSO) δ 8.04 (s, 1H), 7.69-7.62 (m, 1H), 7.57 (s, 1H), 7.54-7.45 (m, 2H), 7.41-7.33 (m, 1H), 7.13 (s, 1H).

Workup

  1. customThe reaction mixture was then partitioned between ethyl acetate
  2. washwashed several times with a saturated aqueous solution of ammonium chloride
  3. customto remove a small amount of di-imidazole material
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-fc2609c1bd5441a59991a499758e5445
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

Loading…