Hydrochloric Acid → 2-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acid

HRID 889540ノート

反応式

HRID 889540 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].O1CCOCC1.[OH-].[Li+].Cl>O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:17])([CH3:16])[CH3:18])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 67971274Methyl 2-chloro-5-(pivalamidomethyl)benzoate

生成物 1

HCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acid収率 77.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Add methyl 2-chloro-5-[(2,2-dimethylpropanoylamino)methyl]benzoate (1.05 kg, 3.7 mol), 1,4-dioxane (5.25 L) and water (3.15 L) together and then add lithium hydroxide (407.8 g, 9.6 mol). Stir the resulting suspension at room temperature for one hour. Acidify the mixture to pH 1 with 5 N aqueous HCl in a dropwise fashion at a rate such that the internal temperature does not exceed 30° C. Concentrate the solution to remove approximately 6 L of solvent, and cool the resulting suspension to 10° C. Filter, wash the resulting solid material with water (8 L), and allow to dry on the sinter for 3 h. Collect the solid, and dry the material in a vacuum oven at 40° C. for 48 h to give the title compound as a free-flowing white solid (775 g, 77.7%). MS (m/z) (35Cl/37Cl) 270/272 (M+1).

後処理

  1. customdoes not exceed 30° C
  2. concentrationConcentrate the solution
  3. customto remove approximately 6 L of solvent
  4. temperaturecool the resulting suspension to 10° C
  5. filtrationFilter
  6. washwash the resulting solid material with water (8 L)
  7. customto dry on the sinter for 3 h
  8. customCollect the solid
  9. customdry the material in a vacuum oven at 40° C. for 48 h

出典と根拠

ORDレコード
ord-f8271c7d666841698eaedbed06ae13b6
出典データセット
uspto-grants-2012_08
特許番号
US08252831B2

反応ノート

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