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

HRID 1934849Notes

Reaction equation

HRID 1934849 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-41e8cb4b2107489198e930d5cb39e912
Source dataset
uspto-grants-2002_05
Patent number
US06384234B1

Reaction notes

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