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

HRID 21728

Reaction equation

HRID 21728 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-4a8947eb6a0041508dc83e1f4689d2d3
Source dataset
uspto-grants-1995_06
Patent number
US05424443

Linked notes

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