Sulfuric Acid → (1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid butyl ester

HRID 250365

반응식

HRID 250365 반응식
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]([OH:15])=[O:14].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)CCC>[CH2:4]([O:14][C:13](=[O:15])[CH2:12][N:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1=[O:1])[CH2:5][CH2:6][CH3:7]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 20825N-PhthaloylglycineHCID 516892Sodium Bicarbonate

생성물 1

HCID 357739(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid butyl ester수율 194.4%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A mixture of 160 ml of butanol, 20.0 g of (1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid (94.6 mmol) and 2.0 ml of concentrated sulfuric acid was refluxed with stirring for 24 h. Then 5 g of sodium bicarbonate were added in portions, stirring continued at r.t. for 5 min and the solvent evaporated in vacuo. The residue was partitioned between 100 ml of water and 100 ml of ethyl acetate. The organic phase was washed with 100 ml of brine, dried over sodium sulfate and was evaporated in vacuo to give a yellowish oil that later solidified. 24.02 g of the title compound were obtained; MS-(+)-ion: M+1=261.9.

후처리

  1. temperaturewas refluxed
  2. stirringstirring
  3. waitcontinued at r.t. for 5 min
  4. customthe solvent evaporated in vacuo
  5. customThe residue was partitioned between 100 ml of water and 100 ml of ethyl acetate
  6. washThe organic phase was washed with 100 ml of brine
  7. dry with materialdried over sodium sulfate
  8. customwas evaporated in vacuo
  9. customto give a yellowish oil that

출처 및 근거

ORD 기록
ord-617796caf49848efaa5247e234cb088c
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863292B2

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