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

HRID 889540노트

반응식

HRID 889540 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f8271c7d666841698eaedbed06ae13b6
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252831B2

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