p-Toluenesulfonic acid monohydrate → HCID 15947181, compound

HRID 1466408Notes

Reaction equation

HRID 1466408 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[N:8]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=3[Cl:24])[CH2:9][C:10]([C:13]([F:16])([F:15])[F:14])(O)[N:11]=2)=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[S:6][C:5]([C:7]2[N:8]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=3[Cl:24])[CH:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[N:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59251584HCID 59251584, compound

Product 1

HCID 15947181HCID 15947181, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 2-(5-bromo-thiophen-2-yl)-1-(2,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-1H-imidazol-4-ol (822 mg, 1.8 mmol) and p-toluenesulfonic acid monohydrate (172 mg, 0.9 mmol) in 10 mL toluene was heated at 120° C. for 6 hrs. The solvent was removed, and the residue was redissolved into dichloromethane, then washed with saturated NaHCO3 and brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by chromatography on silica gel (hexane/EtOAc 85/15) to give an off-white solid (512 mg, 64% yield). 1H-NMR (400 MHz, CDCl3): δ 6.68 (d, 1H), 6.89 (d, 1H), 7.31 (dd, 1H), 7.47 (dd, 1H), 7.55 (d, 1H), 7.56 (s, 1H).

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was redissolved into dichloromethane
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by chromatography on silica gel (hexane/EtOAc 85/15)

Sources & evidence

ORD record
ord-e667c6f4e19942c78be3e871dceb6db1
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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