Sodium Hydroxide → 2-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile

HRID 1862215

反応式

HRID 1862215 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[Sn](Cl)(Cl)(Cl)Cl.[C:24](#[N:32])[C:25]1[C:26](=[CH:28][CH:29]=[CH:30][CH:31]=1)[NH2:27].[OH-].[Na+]>O1CCCC1.C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[N:27][C:26]1[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=1[C:24]#[N:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 5

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 24813Phosphorus oxychlorideHCID 729132-AminobenzonitrileHCID 791761-Benzyl-3-pyrrolidone

生成物 1

HCID 7584062-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile収率 91.1%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

The compound 2-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile (Compound 24) was synthesized by mixing chloroform (25 mL), tetrahydrofuran (25 mL), 1-benzyl-2-pyrrolidinone (5.16 g, 29.4 mmol), phosphorus oxychloride (5.2 mL) and tin(IV) chloride (1.0 mL), stirring at room temperature for 1.5 hours, and adding anthranilonitrile (3.3 g, 27.9 mmol) in portions. The mixture was then stirred at 50° C. for 5 hours under heating and ice-water (15 mL) and 10% aqueous sodium hydroxide solution was added to make weak alkaline. The organic solvent was removed under reduced pressure and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and condensed under vacuum. The crude product was purified by flash chromatography (chloroform-methanol, 100:1) to yield 7.0 g (91%) Compound 24 as slightly yellow needles; mp 59-61° C.; IR (KBr): 2217, 1628, 1439, 1279 cm−1; 1H NMR (DMSO-d6): δ 7.06-7.69 (m, 9H), 4.83 (s, 2H), 3.46 (t, 2H), 2.60 (t, 2H), 2.10 (m, 2H); 13C NMR (CDCl3): δ 162.8, 156.3, 137.6, 133.7, 132.9, 128.7, 128.3, 127.4, 122.8, 121.7, 118.8, 105.9, 48.3, 47.3, 27.7, 19.6. Anal. Calcd. for C18H17N3(275.35): C, 78.52; H, 6.22; N, 15.26. Found: C, 78.37; H, 6.20; N, 15.17.

後処理

  1. customThe compound 2-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile (Compound 24) was synthesized
  2. stirringThe mixture was then stirred at 50° C. for 5 hours
  3. temperatureunder heating
  4. customThe organic solvent was removed under reduced pressure
  5. extractionthe mixture was extracted with chloroform
  6. dry with materialThe extract was dried over anhydrous sodium sulfate and condensed under vacuum
  7. customThe crude product was purified by flash chromatography (chloroform-methanol, 100:1)

出典と根拠

ORDレコード
ord-d679b2dbcb74402c852137a1608f4993
出典データセット
uspto-grants-2003_03
特許番号
US06537993B2

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