Hydrochloric Acid → 4-[N-(4-Methoxybenzoyl)-N-methylamino]benzoic acid

HRID 1242893

반응식

HRID 1242893 반응식
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1.[C:18](Cl)(=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.Cl>O.C1COCC1>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([N:8]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH3:7])=[O:27])=[CH:20][CH:21]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 7477p-Anisoyl chlorideHCID 10340Sodium CarbonateHCID 663454-(Methylamino)benzoic acid

생성물 1

HCID 219397344-[N-(4-Methoxybenzoyl)-N-methylamino]benzoic acid수율 51.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Aqueous solution (50 ml) of sodium carbonate (23 g) was added to THF solution (50 ml) of 4-(methylamino)benzoic acid (5.0 g), and p-anisoyl chloride (5.6 g) was added dropwise to the solution under ice-cooling, which was stirred for 15 minutes, and then stirred at room temperature for 30 minutes. Concentrated hydrochloric acid was added to the reaction mixture under ice-cooling to make the water layer acidic, and extraction was conducted using ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was purified using silica gel column chromatography (development solvent; hexane˜hexane:ethyl acetate=1:2), and recrystallized (ethyl acetate-hexane) to give the titled compound (4.8 g).

후처리

  1. additionwas added dropwise to the solution under ice-
  2. temperaturecooling
  3. stirringstirred at room temperature for 30 minutes
  4. temperaturecooling
  5. extractionextraction
  6. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified
  10. customrecrystallized (ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-04ff0c0dc0be495995be898bf12ede25
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115750B1

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