Chlorosuccinimide → HCID 86037749, compound

HRID 349431Notes

Reaction equation

HRID 349431 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:11]([NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])=[CH:12][S:13][CH:14]=1>C(O)(=O)C>[Cl:1][C:12]1[S:13][CH:14]=[C:10]([Cl:9])[C:11]=1[NH:15][C:16](=[O:21])[C:17]([F:18])([F:20])[F:19]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86597494HCID 86597494, compound

Product 1

HCID 86037749HCID 86037749, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 1.4 g of N-chlorosuccinimide in 25 ml of glacial acetic acid was added dropwise with stirring to a solution of 2.3 g of 4-chloro-3-trifluoroacetylaminothiophene in 60 ml of glacial acetic acid, the mixture was stirred at 40–45° C. for a further 35 minutes and the solvent was distilled off. The residue was admixed with water and extracted with ethyl acetate, the organic phase was washed with water and dried over sodium sulfate, and the solvent was distilled off. The residue was purified by column chromatography on silica gel using a mixture of 10 parts by volume of toluene and 2 parts by volume of n-heptane, and removed from the still unconverted monochloro compound.

Workup

  1. distillationthe solvent was distilled off
  2. extractionextracted with ethyl acetate
  3. washthe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography on silica gel using
  7. additiona mixture of 10 parts by volume of toluene and 2 parts by volume of n-heptane
  8. customremoved from the still unconverted monochloro compound

Sources & evidence

ORD record
ord-392f43cc43b346988baeb9e6f4539748
Source dataset
uspto-grants-2007_02
Patent number
US07179830B2

Reaction notes

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