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

HRID 1934844Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]([S:13]([CH2:16][Cl:17])(=[O:15])=[O:14])[C:10](=[O:12])[CH3:11].[N+:18]([O-])([OH:20])=[O:19]>S(=O)(=O)(O)O.OS(O)(=O)=O.O=S(=O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:18]([O-:20])=[O:19])=[CH:4][C:3]=1[N:9]([S:13]([CH2:16][Cl:17])(=[O:14])=[O:15])[C:10](=[O:12])[CH3:11]

Participants

Conditions

Temperature: 2.5 °C

Procedure

30 g (0.1 mol) of N-(2-chloro-4-fluorophenyl)-N-[(chloromethyl)sulfonyl]acetamide was dissolved in a mixture of 150 mL of concentrated sulfuric acid and 50 mL of 30% oleum with stirring. The mixture was cooled to 0-5° C. and 9.2 mL of the nitrating agent, made from equal volumes of concentrated sulfuric acid and fuming nitric acid, was added slowly keeping the temperature below 5° C. Another 50 mL of oleum and 30 g of the starting material were then added, followed by the further dropwise addition of 9.2 mL of the nitrating agent, allowing the mixture to warm up to 10° C. The mixture was stirred for an additional 40 minutes at 10-15° C. and poured with vigorous stirring onto ice. The precipitated yellow solid was filtered off, washed with water and dried to yield 63.5 g (92%) of the title compound as a solid, which was recrystallized from ethyl acetate, melting at 183-187° C.

Workup

additionwas added slowly
customthe temperature below 5° C
additionfollowed by the further dropwise addition of 9.2 mL of the nitrating agent
temperatureto warm up to 10° C
stirringThe mixture was stirred for an additional 40 minutes at 10-15° C.
additionpoured
stirringwith vigorous stirring onto ice
filtrationThe precipitated yellow solid was filtered off
washwashed with water
customdried

Sources & evidence

ORD record: ord-5df5526100294c8f8bc3b1b11866fc4d
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384234B1

Reaction notes

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