Water → 3-{3-Amino-4-[(trifluoromethyl)thio]phenyl}-5,5-dimethylimidazolidine-2,4-dione

HRID 546576

反応式

HRID 546576 の反応式
[CH3:1][C:2]1([CH3:23])[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+:19]([O-])=O)[CH:9]=2)[C:3]1=[O:22].C(OCC)(=O)C.O.[OH-].[Na+]>Cl.[Zn]>[NH2:19][C:10]1[CH:9]=[C:8]([N:4]2[C:3](=[O:22])[C:2]([CH3:1])([CH3:23])[NH:6][C:5]2=[O:7])[CH:13]=[CH:12][C:11]=1[S:14][C:15]([F:18])([F:16])[F:17]

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67196462HCID 67196462、化合物

生成物 1

HCID 576260173-{3-Amino-4-[(trifluoromethyl)thio]phenyl}-5,5-dimethylimidazolidine-2,4-dione収率 25%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 313Hydrochloric Acid溶媒

反応条件

温度
50 °C

実験手順

To a suspension of 1.75 g of 5,5-dimethyl-3-{3-nitro-4-[(trifluoromethyl)thio]phenyl}imidazolidine-2,4-dione obtained in stage b) below in 60 mL of concentrated hydrochloric acid are added, portionwise, 7.5 g of zinc powder. The reaction mixture is heated at 50° C. for 8 hours and then cooled to room temperature and poured into a mixture of 100 mL of ethyl acetate and 20 mL of water. 5N sodium hydroxide solution is then added to pH 8 and the solid formed is then filtered off through Celite and washed with ethyl acetate. The phases are separated, the aqueous phase is washed with 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 400 mg of 3-{3-amino-4-[(trifluoromethyl)thio]phenyl}-5,5-dimethylimidazolidine-2,4-dione, the characteristics of which are as follows:

後処理

  1. additionare added
  2. temperaturecooled to room temperature
  3. customthe solid formed
  4. filtrationis then filtered off through Celite
  5. washwashed with ethyl acetate
  6. customThe phases are separated
  7. washthe aqueous phase is washed with ethyl acetate
  8. dry with materialthe combined organic phases are dried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue is purified by chromatography on a column of silica
  12. washeluting with a mixture of dichloromethane and methanol (95/5 by volume)

出典と根拠

ORDレコード
ord-477d455a5bdb4bf285de5f0fce4489be
出典データセット
uspto-grants-2011_05
特許番号
US07935819B2

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