Water → 1-Naphthanilide

HRID 905515ノート

反応式

HRID 905515 の反応式
[C:1]1([C:11](Cl)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.[OH-].[NH4+]>C(#N)C.C(OCC)C>[C:15]1([NH:14][C:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[O:12])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

7

反応物 4

HCID 962WaterHCID 6115AnilineHCID 14923Ammonium HydroxideHCID 701461-Naphthalenecarbonyl chloride

生成物 1

HCID 3471821-Naphthanilide収率 82%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
82 °C

実験手順

4.77 g of 1-naphthoyl chloride (TCI America) was dissolved in 100 ml of anhydrous acetonitrile. To the solution so formed, 2.28 ml of aniline (Sigma-Aldrich) was added in a dropwise fashion over a period of c.a. 20 min. The reaction was then refluxed for 2 h at 82° C. 100 ml of distilled water and 5 ml of concentrated ammonium hydroxide were added along with 100 ml of diethyl ether in a separatory funnel. The phases were separated and the aqueous phase was washed with 100 ml of dichloromethane. The organic fractions were collected and dried with magnesium sulfate, filtered and the solvent was then removed under reduced pressure to yield a white solid 5.07 g (82%; 20.5 mmol).

後処理

  1. customTo the solution so formed
  2. custom20 min
  3. customThe phases were separated
  4. washthe aqueous phase was washed with 100 ml of dichloromethane
  5. customThe organic fractions were collected
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was then removed under reduced pressure

出典と根拠

ORDレコード
ord-cb5847bc2b8849bfbcea377930f23d20
出典データセット
uspto-grants-2011_09
特許番号
US08012458B2

反応ノート

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