Hydrochloric Acid → 2-Chloro-N-[3,5-dichloro-4-(6-chlorobenzothiazol-2-yloxy)-phenyl]-4-trifluoromethyl-benzenesulfonamide

HRID 2422436Notes

Reaction equation

HRID 2422436 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:20])[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:12]=2[N:13]=1.Cl[C:22]1[CH:23]=[C:24]([S:32](Cl)(=[O:34])=[O:33])[CH:25]=[CH:26][C:27]=1[C:28]([F:31])([F:30])[F:29].O.[ClH:37]>N1C=CC=CC=1>[Cl:37][C:25]1[CH:26]=[C:27]([C:28]([F:31])([F:30])[F:29])[CH:22]=[CH:23][C:24]=1[S:32]([NH:20][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([O:8][C:9]2[S:10][C:11]3[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:12]=3[N:13]=2)=[C:6]([Cl:19])[CH:5]=1)(=[O:34])=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 221487553-Chloro-4-(trifluoromethyl)benzene-1-sulfonyl chlorideHCID 221487763,5-Dichloro-4-(6-chloro-benzothiazol-2-yloxy)-phenylamine

Product 1

HCID 103038742-Chloro-N-[3,5-dichloro-4-(6-chlorobenzothiazol-2-yloxy)-phenyl]-4-trifluoromethyl-benzenesulfonamideYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3,5-dichloro-4-(6-chloro-benzothiazol-2-yloxy)-phenylamine (102) (2.0 g, 5.79 mmol) and 3-chloro-4-trifluoromethylbenzenesulfonylchloride (1.7 g, 6.08 mmol) in pyridine (10 mL) was stirred at room temperature. After 3 h water was added to the reaction mixture, which was then acidify by 2N HCl. Reaction mixture was extracted twice with AcOEt. Organic layer was washed by brine, dried over MgSO4 and concentrated. Crude residue was purified by column chromatography (H/A=4/1, 80 g of silica gel) to afford title compound 103 (2.11 g, 65%) as a white solid. mp 82-84°. 1H NMR (400 MHz, DMSO-d6) δ 7.32 (2H, s), 7.46 (1H, dd, J=2.2, 8.7 Hz), 7.67 (1H, d, J=8.7 Hz), 8.00 (1H, d, 8.0 Hz), 8.14 (1H, d, J=2.2 Hz), 8.20 (1H, s), 8.38 (1H, d, J=8.3 Hz), 11.6 (1H, br s). MS (M+H) 586

Workup

  1. customReaction mixture
  2. extractionwas extracted twice with AcOEt
  3. washOrganic layer was washed by brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customCrude residue was purified by column chromatography (H/A=4/1, 80 g of silica gel)

Sources & evidence

ORD record
ord-1951f72d420a48909d55a7a73dd4a530
Source dataset
uspto-grants-2011_06
Patent number
US07960408B2

Reaction notes

Loading…