chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide → N-(3-amino-4-fluorophenyl)-1-chloromethanesulfonamide

HRID 1934848Notes

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(O)(=O)C.C(OCC)(=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

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 1-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

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

Sources & evidence

ORD record: ord-8b7518af6321485891ede543f5fefe64
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384234B1

Reaction notes

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