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

HRID 1824410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1824410
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-0ae2063abfa646a797fad919c557631e
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07041691B1

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