Hydrochloric Acid → 2,4-Dichloro-N-[3,5-dichloro-4-(6-chloro-benzothiazol-2-yloxy)-phenyl]benzenesulfonamide

HRID 1835562Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1835562
[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:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[S:29](Cl)(=[O:31])=[O:30].O.Cl>N1C=CC=CC=1>[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[S:29]([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:31])=[O:30]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 221487763,5-Dichloro-4-(6-chloro-benzothiazol-2-yloxy)-phenylamine

Produkt 1

HCID 102095862,4-Dichloro-N-[3,5-dichloro-4-(6-chloro-benzothiazol-2-yloxy)-phenyl]benzenesulfonamideAusbeute 46,4 %

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 2,4-dichloro benzenesulfonylchloride (1.5 g, 6.08 mmol) in pyridine (10 ml) was stirred at room temperature for 12-hr. Water was added to the reaction mixture, which was then acidified 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 (366) (1.49 g, 46%) as a white solid. mp 73-75° 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-2edda9f578ba4606be7b25f1f371f91e
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06770648B2

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