Water → 4-amino-3-chloro-5-methoxyiminomethyl-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)benzamide

HRID 363494

반응식

HRID 363494 반응식
Cl.[NH2:2][C:3]([CH3:10])([CH2:8][CH3:9])[C:4](=[O:7])[CH2:5][Cl:6].O.C(=O)(O)[O-].[Na+].[NH2:17][C:18]1[C:26]([CH:27]=[N:28][O:29][CH3:30])=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][C:19]=1[Cl:31]>C(OCC)(=O)C.C(Cl)Cl>[NH2:17][C:18]1[C:26]([CH:27]=[N:28][O:29][CH3:30])=[CH:25][C:21]([C:22]([NH:2][C:3]([CH2:8][CH3:9])([CH3:10])[C:4](=[O:7])[CH2:5][Cl:6])=[O:23])=[CH:20][C:19]=1[Cl:31]

참가 물질

7

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 183720023-Amino-1-chloro-3-methylpentan-2-one hydrochlorideHCID 544540514-Amino-3-chloro-5-methoxyiminomethylbenzoyl chloride

생성물 1

HCID 541018744-amino-3-chloro-5-methoxyiminomethyl-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)benzamide수율 74%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매2회

실험 절차

In a 5-liter three-necked round bottomed flask was placed 93 g of 3-amino-1-chloro-3-methyl-2-pentanone hydrochloride and 885 mL of water. To the resulting solution were added 138.6 g of sodium bicarbonate followed by 500 mL of ethyl acetate. To the resulting well-stirred mixture was added 123.5 g of 4-amino-3-chloro-5-methoxyiminomethylbenzoyl chloride dissolved in 1000 mL of ethyl acetate at room temperature over a period of 50 minutes. After the addition was complete the reaction mixture was stirred at room temperature for 1 hour. The two phases were separated and the organic layer was washed with water (2×500 mL), brine (1×500 mL), dried over anhydrous magnesium sulfate and the solvent eliminated in a rotary evaporator yielding the crude product as a brown oil. This oil was passed through a short Silica Gel column using methylene chloride as elution solvent. Evaporation of the solvent yielded 133.3 g of the expected 4-amino-3-chloro-5-methoxyiminomethyl-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)benzamide as an off-white solid (mp 140°-141° C.).

후처리

  1. customIn a 5-liter three-necked round bottomed flask was placed
  2. additionAfter the addition
  3. stirringwas stirred at room temperature for 1 hour
  4. customThe two phases were separated
  5. washthe organic layer was washed with water (2×500 mL), brine (1×500 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent eliminated in a rotary evaporator
  8. customyielding the crude product as a brown oil
  9. washas elution solvent
  10. customEvaporation of the solvent

출처 및 근거

ORD 기록
ord-c43967dd536d40baab5500e9ae175741
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05874466

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