Hydrochloric Acid → 4-[2-(1,3-Dioxolan-2-yl)ethyl]benzamide

HRID 2217160노트

반응식

HRID 2217160 반응식
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[OH:16]O.[OH-].[Na+].Cl>CO>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]([NH2:13])=[O:16])=[CH:10][CH:9]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 69219288HCID 69219288, 화합물

생성물 1

HCID 692226804-[2-(1,3-Dioxolan-2-yl)ethyl]benzamide수율 97.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of 4-(2-(1,3-dioxolan-2-yl)ethyl)benzonitrile (1.50 g, 7.34 mmol) (prepared according to the method described in Kelly, S. M., Liquid Crystals 10: 273? 287 (1991)) in MeOH (50 mL) at room temperature were added 30% H2O2 (25.70 mmol) and 6 N NaOH (7.34 mmol) solution. The mixture was warmed to 50? 60? and stirred for 2 h, and to it, 1 N HCl solution was added to adjust to pH 7? 8 at 0?. The MeOH solvent was evaporated off under reduced pressure, and the residue was extracted with CH2Cl2 (3×30 mL). The CH2Cl2 solution was washed with brine (30 mL), dried (anhydrous Na2SO4), filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel using a mixture of MeOH and CH2Cl2 (1:19, then 1:9 (v/v)) as eluent to give 1.58 g (97%) of 4-(2-(1,3-dioxolan-2-yl)ethyl)benzamide as a solid. 1H NMR (400 MHz, CDCl3) δ 7.74 (dd, 2H), 7.29 (d, 2H), 6.01 (br s, 1H), 5.71 (br s, 1H), 4.89 (t, 1H), 3.99 (m, 2H), 3.88 (m, 2H), 2.80 (m, 2H), 1.99 (m, 2H).

후처리

  1. temperatureThe mixture was warmed to 50
  2. customThe MeOH solvent was evaporated off under reduced pressure
  3. extractionthe residue was extracted with CH2Cl2 (3×30 mL)
  4. washThe CH2Cl2 solution was washed with brine (30 mL)
  5. dry with materialdried (anhydrous Na2SO4)
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was purified by MPLC on silica gel using
  9. additiona mixture of MeOH and CH2Cl2 (1:19

출처 및 근거

ORD 기록
ord-8152421fafec42e6bf5c9f0e495d9414
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07407958B2

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