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

HRID 2427238Notes

Reaction equation

HRID 2427238 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 (364) (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-hr 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 365 (2.11 g, 65%) as a white solid. mp 82-84° C.

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-5973071fd09244faa951d46691c3f696
Source dataset
uspto-grants-2011_06
Patent number
US07968567B2

Reaction notes

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