Aniline → 2-(Phenylcarbamoyl)acetic acid

HRID 418567

反応式

HRID 418567 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](Cl)(C)C.CC1(C)[O:19][C:18](=O)[CH2:17][C:16](=[O:21])[O:15]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:19]=[C:18]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:17][C:16]([OH:21])=[O:15]

参加物

6

反応物 4

HCID 6115AnilineHCID 6397ChlorotrimethylsilaneHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 516892Sodium Bicarbonate

生成物 1

HCID 2565932-(Phenylcarbamoyl)acetic acid収率 65.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of aniline (13 mL, 143 mmol) in DCM (290 mL) was added TMSCl (18.2 mL, 143 mmol) at room temperature and the reaction mixture was stirred for 1 hour. [Rigo, B.; Fasseur, D.; Cauliez, P. and Couturier, D. Tetrahedron Lett.; 30; 23; 1989; 3073-3076.]. 2,2-Dimethyl-1,3-dioxane-4,6-dione (20.6 g, 143 mmol) was added and combined reaction mixture was stirred overnight at room temperature, poured into saturated NaHCO3 solution and extracted with EtOAc. The aqueous phase was collected, acidified with conc. HCl to pH-3 by addition of 2N HCl and extracted with DCM. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure affording 3-oxo-3-(phenylamino)propanoic acid (1, 16.82 g, 65% yield) as a white solid. MS (m/z): 180.0 (25%) (M+H), 202.0 (100%) (M+Na).

後処理

  1. customreaction mixture
  2. stirringwas stirred overnight at room temperature
  3. extractionextracted with EtOAc
  4. customThe aqueous phase was collected
  5. additionacidified with conc. HCl to pH-3 by addition of 2N HCl
  6. extractionextracted with DCM
  7. dry with materialThe organic phase was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-baa6e897110f425db32b695f5894c54a
出典データセット
uspto-grants-2012_01
特許番号
US08093264B2

関連ノート

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