Chlorosuccinimide → HCID 22404752, compound

HRID 440696Notes

Reaction equation

HRID 440696 reaction equation
[NH2:1][C:2]1[C:11]2[O:10][C:9]([CH3:13])([CH3:12])[CH:8]=[CH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[F:14].[Cl:15]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[C:11]2[O:10][C:9]([CH3:12])([CH3:13])[CH:8]=[CH:7][C:6]=2[C:5]([Cl:15])=[CH:4][C:3]=1[F:14]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 22404809HCID 22404809, compound

Product 1

HCID 22404752HCID 22404752, compoundYield 329.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By a method analogous to that of Example 11, Step J, 1.5 grams (0.0008 mole) of 8-amino-2,2-dimethyl-7-fluoro-2H-1-benzopyran was reacted with 1.1 grams (0.008 mole) of N-chlorosuccinimide in 50 mL of N,N-dimethylformamide. The crude reaction product was purified with column chromatography on silica gel, with hexane and 1:1 methylene chloride:hexane hexane as the eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.6 gram of 8-amino-5-chloro-2,2-dimethyl-7-fluoro-2H-1-benzopyran. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThe crude reaction product
  2. customwas purified with column chromatography on silica gel, with hexane and 1:1 methylene chloride
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1e9d4033041b4337a0b387e08a61868d
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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