p-Toluenesulfonic acid → HCID 57470286, compound

HRID 1672995Notes

Reaction equation

HRID 1672995 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10](=[NH:12])[CH3:11].C(=O)(O)[O-].[Na+].Br[CH2:19][C:20](=O)[C:21]([F:24])([F:23])[F:22].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH:19]=[C:20]([C:21]([F:24])([F:23])[F:22])[N:12]=[C:10]1[CH3:11]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium BicarbonateHCID 178465580HCID 178465580, compound

Product 1

HCID 57470286HCID 57470286, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

A 500 mL flask was charged with 4.8 g (24 mmol) of N-(2,6-dichlorophenyl)acetamidine, sodium bicarbonate 4.03 g (48 mmol) and 250 mL anhydrous ethanol. 5 g (26.2 mmol) of 3-bromo-1,1,1-trifluoro-propan-2-one was added dropwise. After 1 h solid was filtered off and the filtrate was evaporated in vacuo to give a crude. A mixture of the crude and p-toluenesulfonic acid (668 mg, 3.5 mmol) in toluene was heated to 105° C. for 15 hours. The crude reaction mixture was washed into a separatory funnel with ethyl acetate and water. The organic layer was separated, washed with brine, dried (Na2SO4), and concentrated in vacuo to give the crude product, which was then purified by column chromatography on silica eluting with EtOAc-Hexane (10:0 to 3:2) to afford 1-(2,6-dichloro-phenyl)-2-methyl-4-trifluoromethyl-1H-imidazole as a tan solid (0.9, 43%); 1H NMR (400 MHz, CDCl3): δ 7.52 (m, 2H), 7.43 (m, 1H), 7.19 (m, 1H), 2.2 (s, 3H); MS (ES): 295 [M+H]+.

Workup

  1. filtrationAfter 1 h solid was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customto give a crude
  4. customThe crude reaction mixture
  5. washwas washed into a separatory funnel with ethyl acetate and water
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customto give the crude product, which
  11. customwas then purified by column chromatography on silica eluting with EtOAc-Hexane (10:0 to 3:2)

Sources & evidence

ORD record
ord-f3a2d75c903a4f009c0bb75833de5eec
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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