Chlorosuccinimide → HCID 18916431, compound

HRID 1290634Notes

Reaction equation

HRID 1290634 reaction equation
[NH2:1][C:2]1[C:10]2[S:9][C:8]([Cl:11])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[Cl:12].[Cl:13]N1C(=O)CCC1=O.[Cl-].[Li+]>CN(C)C=O>[NH2:1][C:2]1[C:10]2[S:9][C:8]([Cl:11])=[N:7][C:6]=2[C:5]([Cl:13])=[CH:4][C:3]=1[Cl:12]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 433294Lithium ChlorideHCID 18916443HCID 18916443, compound

Product 1

HCID 18916431HCID 18916431, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere a solution of 6.0 grams (27 mmole) of 7-amino-2,6-dichlorobenzothiazole in 75 mL of N,N-dimethylformamide was stirred and cooled in an ice bath. To this was then added 4.3 grams (32 mmole) of N-chlorosuccinimide. Upon completion of the addition the reaction mixture was stirred for 20 minutes and then warmed to ambient temperature and stirred for an additional 18 hours. After this time the reaction mixture was poured into 250 mL of ice-water, and about 15 grams of lithium chloride was added, after which the reaction mixture was stirred for 30 minutes. The resulting precipitate was collected by filtration and dried under reduced pressure, yielding a dark solid, which was purified by column chromatography on silica gel. Elution was accomplished with 4:1 hexane:ethyl acetate. The product-containing fractions were combined and concentrated under reduced pressure, yielding 4.4 grams of 7-amino-2,4,6-trichlorobenzothiazole. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturecooled in an ice bath
  2. additionUpon completion of the addition the reaction mixture
  3. stirringstirred for an additional 18 hours
  4. additionwas added
  5. stirringafter which the reaction mixture was stirred for 30 minutes
  6. filtrationThe resulting precipitate was collected by filtration
  7. customdried under reduced pressure
  8. customyielding a dark solid, which
  9. customwas purified by column chromatography on silica gel
  10. washElution
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7d7635bf3c124fc0a3eeafd18835bf3f
Source dataset
uspto-grants-1998_05
Patent number
US05753595

Reaction notes

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