Chlorosuccinimide → HCID 22404747, compound

HRID 440699Notes

Reaction equation

HRID 440699 reaction equation
[NH2:1][C:2]1[C:11]2[O:10][C:9]([CH3:13])([CH3:12])[CH2:8][CH2:7][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])[CH2:8][CH2:7][C:6]=2[C:5]([Cl:15])=[CH:4][C:3]=1[F:14]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 22404749HCID 22404749, compound

Product 1

HCID 22404747HCID 22404747, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By a method analogous to that of Example 11, Step J, 6.7 grams (0.034 mole) of 8-amino-3,4-dihydro-2,2-dimethyl-7-fluoro-2H-1-benzopyran was reacted with 4.6 grams (0.035 mole) of N-chlorosuccinimide in 100 mL of N,N-dimethylformamide. The crude reaction product was purified with column chromatography on silica gel, with hexane and 1:4 methylene chloride:hexane as the eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding 4.0 grams of 8-amino-5-chloro-3,4-dihydro-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 1:4 methylene chloride
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a83ab7a9712b4172a8746f98f8adde0c
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

Loading…