Hydrochloric Acid → 2-[2-(4-Trifluoromethyl-phenoxymethyl)-1h-benzoimidazol-5-yl]-benzenesulfonamide hydrochloride salt

HRID 1433185Notes

Reaction equation

HRID 1433185 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:29]=[CH:28][C:6]([O:7][CH2:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[S:24]([NH2:27])(=[O:26])=[O:25])=[CH:17][C:11]=3[N:10]=2)=[CH:5][CH:4]=1.[ClH:32]>CCOC(C)=O>[ClH:32].[F:31][C:2]([F:1])([F:30])[C:3]1[CH:29]=[CH:28][C:6]([O:7][CH2:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[S:24]([NH2:27])(=[O:26])=[O:25])=[CH:17][C:11]=3[N:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178514703HCID 178514703, compound

Product 1

HCID 1784795952-[2-(4-Trifluoromethyl-phenoxymethyl)-1h-benzoimidazol-5-yl]-benzenesulfonamide hydrochloride saltYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide (19 g, 42.5 mmol) was dissolved in EtOAc (1000 mL) with warming to near boiling for complete dissolution. To the stirred solution at rt (orange in color) was added aqueous HCl (1 N, 850 mL, 20 eq.) all at once. The resulting suspension was stirred for 30 min at room temperature. The solid was filtered, washed with a small amount of EtOAc and water. The solid was dried in a high vacuum (2 torr) oven at 45° C. for 16 h, to provide (15.71 g) of the title compound in 77% yield. Calculated C21H16N3O3F3S×1.0 HCl×0.08H2O: C, 51.97; H, 3.56; N, 8.66; Cl 7.30; F 11.74; S 6.61; KF 0.30 Found: C, 52.11; H, 3.38; N, 8.37; Cl 7.43; F 11.53; S 6.56; KF 0.27

Workup

  1. temperaturewith warming
  2. dissolutionfor complete dissolution
  3. filtrationThe solid was filtered
  4. washwashed with a small amount of EtOAc and water
  5. customThe solid was dried in a high vacuum (2 torr) oven at 45° C. for 16 h

Sources & evidence

ORD record
ord-a7f2e45abf09461cafd7b3c2e4827c9d
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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