Chlorosuccinimide → HCID 18966289, compound

HRID 2226103Notes

Reaction equation

HRID 2226103 reaction equation
[NH2:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[F:12].[Cl:13]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[C:5]([Cl:13])=[CH:4][C:3]=1[F:12]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 189662856-Fluoro-2,3-dihydro-1,4-benzodioxin-5-amine

Product 1

HCID 18966289HCID 18966289, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In a flask were placed 3.05 g (0.018 mole) of 5-amino-6-fluoro-1,4-benzodioxane and 40 mL of N,N-dimethylformamide. To this solution was added in a dropwise manner a solution of 2.65 g (0.0198 mole) of N-chlorosuccinimide in N,N-dimethylformamide while maintaining the temperature at ambient conditions. The solvent was evaporated under reduced pressure, leaving a residue which was passed through a column of silica gel, eluting with methylene chloride/heptane (1:1 ). Product-containing fractions were combined and the solvent evaporated, yielding 2.25 g of 5-amino-8-chloro-6-fluoro-1,4-benzodioxane as the residue. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customIn a flask were placed
  2. temperaturewhile maintaining the temperature at ambient conditions
  3. customThe solvent was evaporated under reduced pressure
  4. customleaving a residue which
  5. washeluting with methylene chloride/heptane (1:1 )
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-c51b320f636d46019a029b60b4925189
Source dataset
uspto-grants-1994_09
Patent number
US05346881

Reaction notes

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