Chlorosuccinimide → N-(5-amino-2-chloro4-fluorophenyl)-1-chloromethanesulfonamide

HRID 432967Notes

Reaction equation

HRID 432967 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][S:10]([CH2:13][Cl:14])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].[Cl:15]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([Cl:15])=[C:4]([NH:9][S:10]([CH2:13][Cl:14])(=[O:11])=[O:12])[CH:3]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 18760845N-(3-amino-4-fluorophenyl)-1-chloromethanesulfonamide

Product 1

HCID 11000212N-(5-amino-2-chloro4-fluorophenyl)-1-chloromethanesulfonamideYield 82.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-(3-amino-4-fluorophenyl)-1-chloromethanesulfonamide (4.42 g, 18.5 mmol), N-chlorosuccinimide (2.47 g) in 50 mL of anhydrous dimethylformamide was heated to 50° C. for 1.5 hours. The reaction mixture was diluted with 200 mL of ethyl acetate and washed with water (twice with 50 mL). The organic phase was separated, dried (MgSO4), and concentrated under reduced pressure to yield 4.15 g (82%) of the title compound. Purification by flash chromatography provided a solid melting at 107-108° C.

Workup

  1. washwashed with water (twice with 50 mL)
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ba475d7c883140938a77ac0c2be3d524
Source dataset
uspto-grants-2003_12
Patent number
US06664400B2

Reaction notes

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