Water → 3,5-dichloro-N-(3,3-dichloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide

HRID 363486Notes

Reaction equation

HRID 363486 reaction equation
Cl.[NH2:2][C:3]([CH3:11])([CH2:9][CH3:10])[C:4](=[O:8])[CH:5]([Cl:7])[Cl:6].O.C(=O)(O)[O-].[Na+].[Cl:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([Cl:29])[C:27]=1[CH3:28])[C:22](Cl)=[O:23]>C(OCC)(=O)C>[Cl:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([Cl:29])[C:27]=1[CH3:28])[C:22]([NH:2][C:3]([CH2:9][CH3:10])([CH3:11])[C:4](=[O:8])[CH:5]([Cl:7])[Cl:6])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 111279193,5-Dichloro-4-methylbenzoyl chlorideHCID 183720063-Amino-1,1-dichloro-3-methyl-2-pentanone hydrochloride

Product 1

HCID 158388443,5-dichloro-N-(3,3-dichloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamideYield 85.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In a 100 mL three-necked round bottomed flask was placed 0.93 g of 3-amino-1,1-dichloro-3-methyl-2-pentanone hydrochloride and 5 mL of water. To the resulting solution was added 0.76 g of sodium bicarbonate followed by 20 mL of ethyl acetate. To the resulting well-stirred mixture was added 0.94 g of 3,5-dichloro-4-methylbenzoyl chloride dissolved in 20 mL of ethyl acetate at room temperature over a period of 5 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 (2×25 mL), brine (1×25 mL), dried over anhydrous magnesium sulfate and the solvent removed using a rotary evaporator yielding 1.34 g (84% yield) of 3,5-dichloro-N-(3,3-dichloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide as a white solid. This solid was used as such in the following step.

Workup

  1. customIn a 100 mL 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 (2×25 mL), brine (1×25 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent removed
  8. customa rotary evaporator

Sources & evidence

ORD record
ord-4e164f935be24e48a1deb2ea993d2c24
Source dataset
uspto-grants-1999_02
Patent number
US05874466

Reaction notes

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