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

HRID 546577
ノート
印刷プレビュー

反応式

HRID 546577 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 222AmmoniaHCID 944Nitric AcidHCID 132680685,5-Dimethyl-3-{4-[(trifluoromethyl)sulfanyl]phenyl}imidazolidine-2,4-dione

生成物 1

HCID 671964625,5-Dimethyl-3-{3-nitro-4-[(trifluoromethyl)thio]phenyl}imidazolidine-2,4-dione

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒2 回

反応条件

温度
0 °C

実験手順

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:

後処理

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

出典と根拠

ORDレコード
ord-16bdf6010c1c4de4aa7c3fd81dbe86e6
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07935819B2

反応ノート

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