Chlorine → HCID 53685228, compound

HRID 1981339Notes

Reaction equation

HRID 1981339 reaction equation
[Cl:1]Cl.[CH3:3][CH:4]1[C:8]2[CH:9]=[CH:10][C:11]([N:13]([CH3:18])[CH:14]([CH2:16][CH3:17])[CH3:15])=[CH:12][C:7]=2[O:6][C:5]1=[O:19]>C(Cl)(Cl)Cl>[Cl:1][C:10]1[C:11]([N:13]([CH3:18])[CH:14]([CH2:16][CH3:17])[CH3:15])=[CH:12][C:7]2[O:6][C:5](=[O:19])[CH:4]([CH3:3])[C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 53803863HCID 53803863, compound

Product 1

HCID 53685228HCID 53685228, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A cold solution of chlorine in chloroform is added dropwise at 0° to 5° C., while stirring, to a mixture of 14.7 g (0.063 mole) of 3-methyl-6-(N-methyl-N-2-butylamino)-benzofuran-2(3H)-one in 100 ml of chloroform until no more educt is visible in the thin layer chromatograph. The reaction mixture is washed with methylene chloride, dilute sodium bicarbonate solution and water. The crude product remaining after drying and concentration by evaporation of the organic phase is chromatographed over silica gel with petroleum ether/ether. Recrystallisation of the pure fractions from ether/petroleum ether yields 5-chloro-3-methyl-6-(N-methyl-N-2-butylamino)-benzofuran-2(3H)-one in the form of a colourless oil, b.p. 0.05, 190° C.

Workup

  1. washThe reaction mixture is washed with methylene chloride, dilute sodium bicarbonate solution and water
  2. customafter drying
  3. concentrationconcentration
  4. customby evaporation of the organic phase
  5. customis chromatographed over silica gel with petroleum ether/ether
  6. customRecrystallisation of the pure fractions from ether/petroleum ether

Sources & evidence

ORD record
ord-11a8a08c28434db08c00bcc5f40243c6
Source dataset
uspto-grants-1985_04
Patent number
US04514415

Reaction notes

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