Thiophosgene → 2,4-Dichloro-6-fluoro-7-isothiocyanatobenzothiazole

HRID 21728

Reaktionsgleichung

Reaktionsgleichung von HRID 21728
C(=O)([O-])[O-].[Ca+2].[C:6](Cl)(Cl)=[S:7].[NH2:10][C:11]1[C:19]2[S:18][C:17]([Cl:20])=[N:16][C:15]=2[C:14]([Cl:21])=[CH:13][C:12]=1[F:22]>O.ClCCl>[Cl:20][C:17]1[S:18][C:19]2[C:11]([N:10]=[C:6]=[S:7])=[C:12]([F:22])[CH:13]=[C:14]([Cl:21])[C:15]=2[N:16]=1

Komponenten

6

Edukt 3

HCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 199334577-Amino-2,4-dichloro-6-fluorobenzothiazole

Produkt 1

HCID 199334642,4-Dichloro-6-fluoro-7-isothiocyanatobenzothiazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A suspension of 16.9 g calcium carbonate in 100 ml water was added to a solution of 19.4 g thiophosgene in 100 ml dichloromethane. A solution of 40 g 7-amino-2,4-dichloro-6-fluorobenzothiazole in 500 ml dichloromethane was added, dropwise at 5° C., and the mixture stirred for 8 hours at room temperature. The solid was filtered, the phases were separated, and the organic phase dried over magnesium sulfate and concentrated. The residue was purified by column chromatography (eluent: hexane/ethyl acetate). Yield: 16 g=38% of theory m.p.: 80°-81° C.

Aufarbeitung

  1. filtrationThe solid was filtered
  2. customthe phases were separated
  3. dry with materialthe organic phase dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (eluent: hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4a8947eb6a0041508dc83e1f4689d2d3
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424443

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