Bromine → HCID 53712515, compound

HRID 620932Notes

Reaction equation

HRID 620932 reaction equation
[CH2:1]([S:3]([CH2:6][C:7](=[O:22])[C:8]([NH:11][C:12](=[O:21])[C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=1)([CH3:10])[CH3:9])(=[O:5])=[O:4])[CH3:2].[Br:23]Br>C(Cl)Cl.BrBr>[CH2:1]([S:3]([CH:6]([Br:23])[C:7](=[O:22])[C:8]([NH:11][C:12](=[O:21])[C:13]1[CH:14]=[C:15]([Cl:20])[CH:16]=[C:17]([Cl:19])[CH:18]=1)([CH3:10])[CH3:9])(=[O:5])=[O:4])[CH3:2]

Participants

5

Reactant 2

HCID 24408BromineHCID 53720030HCID 53720030, compound

Product 1

HCID 53712515HCID 53712515, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 24408BromineCatalystHCID 6344DichloromethaneSolvent

Procedure

N-(3'-Ethylthio-1',1'-dimethylacetonyl)-3,5-dichlorobenzamide (5.0 gm, 0.015 m) was taken in chloroform (200 ml) and meta-chloroperbenzoic acid (7.8 gm, 0.045 m) was added with stirring at room temperature for about 16 hours. The reaction mixture was transferred, with the use of ether (200 ml) as a rinse, to a separatory funnel. The organic solution was washed sequentially with sodium sulfite (2×100 ml), sodium bicarbonate (200 ml), water (100 ml) and brine (200 ml). The solvent was removed after drying over anhydrous sodium sulfate. Recrystallization using ethyl acetate and hexane (1:4) afforded 4.3 gm of 3-(3',5'-dichlorobenzoylamino)-2-oxo-3-methylbutyl ethyl sulfone. A portion of this sulfone (1.00 gm, 0.0027 mole) was taken in methylene chloride (50 ml) and bromine (0.13 ml, 0.003 mole) was added in one portion. Another 2-3 drops of bromine were added and the mixture was heated to reflux for about 1 hour. The solvent was removed and the resulting oil was recrystallized from hexane to obtain 800 mg of the desired product.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for about 1 hour
  3. customThe solvent was removed
  4. customthe resulting oil was recrystallized from hexane

Sources & evidence

ORD record
ord-100d449289dc4fcfa8ea717fb902fcec
Source dataset
uspto-grants-1989_04
Patent number
US04822902

Reaction notes

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