Trifluoroacetic acid → HCID 11517942, compound

HRID 2112989Notes

Reaction equation

HRID 2112989 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:11]([C:17]([O:19]C(C)(C)C)=[O:18])[N:10]=[C:9]2[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.[SiH](CC)(CC)CC>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:11]([C:17]([OH:19])=[O:18])[N:10]=[C:9]2[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 11598558HCID 11598558, compound

Product 1

HCID 11517942HCID 11517942, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of tert-butyl 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfonyl-1H-imidazole-4-carboxylate (4.76 g, 9.49 mmol) in CH2Cl2 (60 ml) was added excess TFA (9.40 ml, 0.2124 mol) and Et3SiH (3.8 ml, 0.0238 mol). The solution was reacted at room temperature for 16 h and concentrated in vacuo. Water was added and the formed precipitate was collected by filtration and subsequently dried to give 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfonyl-1H-imidazole-4-carboxylic acid in quantitative yield, mp ˜130° C. (dec); 1H-NMR (400 MHz, CDCl3) δ 3.45 (s, 3H), 3.50 (br s, 1H), 7.40 (br d, J˜8 Hz, 2H), 7.42 (dd, J=8 and 2 Hz, 1H), 7.50 (br d, J˜8 Hz, 2H), 7.59 (d, J=2 Hz, 1H), 7.61 (d, J=8 Hz, 1H). Analogously was prepared 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfinyl-1H-imidazole-4-carboxylic acid 1H-NMR (400 MHz, CDCl3) δ 2.99 (s, 3H), 7.37-7.60 (m, 7H), 13.20 (br s, 1H).

Workup

  1. customThe solution was reacted at room temperature for 16 h
  2. concentrationconcentrated in vacuo
  3. additionWater was added
  4. filtrationthe formed precipitate was collected by filtration
  5. customsubsequently dried

Sources & evidence

ORD record
ord-b49d5bab9a9644c5a9b7248a0e4be73c
Source dataset
uspto-grants-2009_04
Patent number
US07524867B2

Reaction notes

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