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

HRID 1934845Notes

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 wag 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-a94c93d2248541529d760ec239990601
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384234B1

Reaction notes

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