Ethyl Acetate → N-(3-amino-4-fluorophenyl)-1-chloromethanesulfonamide

HRID 432966Notes

Reaction equation

HRID 432966 reaction equation
[Cl:1][CH2:2][S:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([N+:14]([O-])=O)[CH:8]=1)(=[O:5])=[O:4].C(OCC)(=O)C>C(O)(=O)C.[Fe]>[NH2:14][C:9]1[CH:8]=[C:7]([NH:6][S:3]([CH2:2][Cl:1])(=[O:4])=[O:5])[CH:12]=[CH:11][C:10]=1[F:13]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 18760842chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide

Product 1

HCID 18760845N-(3-amino-4-fluorophenyl)-1-chloromethanesulfonamideYield 94%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 12.5 g of iron powder (223 mmol) and 16 mL of an aqueous solution of acetic acid (8%) was heated to 80° C., and a solution of 6 g of I -chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide (22.3 mmol) in 20 mL of glacial acetic acid and 22 mL ethyl acetate was added dropwise to the mixture. After heating for 1.5 h the reaction mixture was filtered through a pad of Celite® and washed with 200 mL of ethyl acetate and water (twice with 25 mL). The organic phase was separated, dried (MgSO4), filtered and concentrated under reduced pressure to yield 5 g (94%) of the title compound as a solid melting at 128-129° C.

Workup

  1. temperatureAfter heating for 1.5 h the reaction mixture
  2. filtrationwas filtered through a pad of Celite®
  3. washwashed with 200 mL of ethyl acetate and water (twice with 25 mL)
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bef168359c1344ba9cf349bd425414a3
Source dataset
uspto-grants-2003_12
Patent number
US06664400B2

Reaction notes

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