N-(2-chloro-4-fluoro-5-nitrophenyl)-N-[(chloromethyl)sulfonyl]acetamide → N-(5-amino-2-chloro-4-fluorophenyl)-N-[(chloromethyl)sulfonyl]acetamide

HRID 432963Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[N:12]([S:16]([CH2:19][Cl:20])(=[O:18])=[O:17])[C:13](=[O:15])[CH3:14]>C(O)C.[Ir]>[NH2:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([Cl:1])=[C:3]([N:12]([S:16]([CH2:19][Cl:20])(=[O:18])=[O:17])[C:13](=[O:15])[CH3:14])[CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

65.7 g (0.19 mol) of N-(2-chloro-4-fluoro-5-nitrophenyl)-N-[(chloromethyl)sulfonyl]acetamide were dissolved in 1200 mL of ethanol and transferred into an autoclave. 2.5 g of an iridium catalyst (5% on carbon) were added and the apparatus was purged with nitrogen and hydrogen, respectively. A hydrogen pressure of 2,000 kPa (20 atmospheres) was applied and the mixture was heated to 80° C. After 4 hours the hot reaction mixture was filtered and cooled to room temperature whereas some of the product precipitated. The crystals were filtered off and the mother liquor was concentrated and cooled. The precipitates were combined and dried to yield 41.9 g (70.2%) of the title compound as a solid melting at 176-180° C.

Workup

customthe apparatus was purged with nitrogen and hydrogen
filtrationAfter 4 hours the hot reaction mixture was filtered
temperaturecooled to room temperature whereas some of the product
customprecipitated
filtrationThe crystals were filtered off
concentrationthe mother liquor was concentrated
temperaturecooled
customdried

Sources & evidence

ORD record: ord-84a5692fec5645e790ca31af5849f2af
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06664400B2

Reaction notes

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