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

HRID 1586576Notes

Reaction equation

HRID 1586576 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-3ba6b4256a5e4d60880bd915738597c8
Source dataset
uspto-grants-1999_08
Patent number
US05945565

Reaction notes

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