Chlorosuccinimide → HCID 70300013, compound

HRID 1421851Notes

Reaction equation

HRID 1421851 reaction equation
[NH2:1][C:2]1[C:10]2[O:9][NH:8][CH:7]([CH3:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[F:12].[Cl:13]N1C(=O)CCC1=O.[Cl-].[Li+]>CN(C=O)C>[NH2:1][C:2]1[C:10]2[O:9][NH:8][CH:7]([CH3:11])[C:6]=2[C:5]([Cl:13])=[CH:4][C:3]=1[F:12]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 433294Lithium ChlorideHCID 70295985HCID 70295985, compound

Product 1

HCID 70300013HCID 70300013, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 7-amino-6-fluoro-3-methyl-1,2(2H)-benzisoxazole (3.5 g, 0.021 mole) in DMF (50 mL) was stirred, and a solution of N-chlorosuccinimide (2.8 g, 0.02 mole) in a minimum amount of DMF was added dropwise. Upon completion of addition, the reaction mixture was stirred for about 18 hours. After this time, the reaction mixture was poured into aqueous 10% lithium chloride and then thoroughly extracted with ether. The combined extracts were washed with aqueous 10% lithium chloride, dried with magnesium sulfate, and concentrated to a residue. The residue was subjected to silica gel column chromatography using 9:1 to 4:1 hexane and ethyl acetate to provide 2.6 grams of 7-amino-4-chloro-6-fluoro-3-methyl-1,2(2H)-benzisoxazole. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. extractionthoroughly extracted with ether
  3. washThe combined extracts were washed with aqueous 10% lithium chloride
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated to a residue

Sources & evidence

ORD record
ord-ce1f44a159e945f0ba86d02b41d4ec2d
Source dataset
uspto-grants-2000_06
Patent number
US06080702

Reaction notes

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