Ammonia → 5,5-Dimethyl-3-{3-nitro-4-[(trifluoromethyl)thio]phenyl}imidazolidine-2,4-dione

HRID 546577Notes

Reaction equation

[CH3:1][C:2]1([CH3:20])[NH:6][C:5](=[O:7])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)[C:3]1=[O:19].[N+:21]([O-])([OH:23])=[O:22].N>S(=O)(=O)(O)O>[CH3:1][C:2]1([CH3:20])[NH:6][C:5](=[O:7])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]([F:18])([F:17])[F:16])=[C:10]([N+:21]([O-:23])=[O:22])[CH:9]=2)[C:3]1=[O:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3.8 g of 5,5-dimethyl-3-{4-[(trifluoro-methyl)thio]phenyl}imidazolidine-2,4-dione obtained in stage a) below in 7 mL of concentrated sulphuric acid is added dropwise at −5° C. a mixture of nitric acid (0.75 mL) in 3 mL of concentrated sulphuric acid. After stirring for 4 hours at 0° C. (ice bath) the mixture is poured onto 150 g of ice and the pH is raised to 10 by addition of concentrated aqueous ammonia. The aqueous phase is then extracted with twice 150 mL of ethyl acetate and the combined organic phases are dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a mixture of dichloromethane and methanol (95/5 by volume) to give 1.8 g of 5,5-dimethyl-3-{3-nitro-4-[(trifluoromethyl)thio]phenyl}imidazolidine-2,4-dione, the characteristics of which are as follows:

Workup

extractionThe aqueous phase is then extracted with twice 150 mL of ethyl acetate
dry with materialthe combined organic phases are dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue is purified by chromatography on a column of silica
washeluting with a mixture of dichloromethane and methanol (95/5 by volume)

Sources & evidence

ORD record: ord-16bdf6010c1c4de4aa7c3fd81dbe86e6
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935819B2

Reaction notes

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