Hydrochloric Acid → 4-(4,4-Dimethyl-2,5-dioxoimidazolidin-1-yl)-2-pentafluorosulfanylbenzonitrile

HRID 2356664ノート

反応式

HRID 2356664 の反応式
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([S:10]([F:15])([F:14])([F:13])([F:12])[F:11])[CH:3]=1.ClC(Cl)(O[C:20](=[O:26])OC(Cl)(Cl)Cl)Cl.Cl.[NH2:29][C:30]([CH3:39])([CH3:38])[C:31](OC(C)(C)C)=[O:32]>O1CCCC1.C(OCC)(=O)C.O.C(N(CC)CC)C>[CH3:38][C:30]1([CH3:39])[C:31](=[O:32])[N:1]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([S:10]([F:15])([F:11])([F:12])([F:13])[F:14])[CH:3]=2)[C:20](=[O:26])[NH:29]1

参加物

9

反応物 4

HCID 313Hydrochloric Acid2 回HCID 94429TriphosgeneHCID 7019940tert-Butyl 2-methylalaninateHCID 596421594-Amino-2-pentafluorosulfanylbenzonitrile

生成物 1

HCID 582571594-(4,4-Dimethyl-2,5-dioxoimidazolidin-1-yl)-2-pentafluorosulfanylbenzonitrile収率 41%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
5 °C

実験手順

To prepare compound 51.1, the procedure may be according to process “A”. 505 mg of amine 51.9 and 227.1 mg of triphosgene were dissolved in 15 ml of dry tetrahydrofuran. At 0° C., over 30 minutes, 0.864 ml of triethylamine in 2.5 ml of tetrahydrofuran was added dropwise and then the mixture was stirred at 5° C. for a further 10 minutes. 404.7 mg of the hydrochloride of tert-butyl 2-amino-2-methylpropionate were added, and the mixture was allowed to warm to room temperature and stirred at room temperature for a further 2 h. The reaction mixture was admixed with 2.5 ml of concentrated hydrochloric acid and stirred at room temperature for a further 2 h. For workup, the mixture was admixed with water and ethyl acetate, and the organic phase was removed, washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The chromatographic purification was effected according to method [RP1]. The product-containing fractions were concentrated under reduced pressure, the residue was extracted by repeated shaking with dichloromethane, and the organic phase was dried over magnesium sulfate and concentrated under reduced pressure. 51.1 was obtained in 41% yield. 1H NMR: 8.85, s, 1H, 8.4, s, 1H, 8.3, d, 1H, 8.02, d, 1H, 1.4, s, 6H.

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred at room temperature for a further 2 h
  3. stirringstirred at room temperature for a further 2 h
  4. customthe organic phase was removed
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe chromatographic purification
  10. concentrationThe product-containing fractions were concentrated under reduced pressure
  11. extractionthe residue was extracted
  12. stirringby repeated shaking with dichloromethane
  13. dry with materialthe organic phase was dried over magnesium sulfate
  14. concentrationconcentrated under reduced pressure
  15. custom51.1 was obtained in 41% yield

出典と根拠

ORDレコード
ord-38f8e43012e549beb718ece04a46e38e
出典データセット
uspto-grants-2010_07
特許番号
US07759366B2

反応ノート

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