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

HRID 1242893

反応式

HRID 1242893 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-04ff0c0dc0be495995be898bf12ede25
出典データセット
uspto-grants-2006_10
特許番号
US07115750B1

関連ノート

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