Chlorine → HCID 13576946, compound

HRID 544712Notes

Reaction equation

HRID 544712 reaction equation
[Cl:1]Cl.[CH3:3][CH:4]1[C:8]2[CH:9]=[CH:10][C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:12][C:7]=2[O:6][C:5]1=[O:19]>C(Cl)(Cl)Cl.C(Cl)Cl>[Cl:1][C:10]1[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:12][C:7]2[O:6][C:5](=[O:19])[CH:4]([CH3:3])[C:8]=2[CH:9]=1

Participants

5

Reactant 2

HCID 24526ChlorineHCID 135769393-Methyl-6-(morpholin-4-yl)-1-benzofuran-2(3H)-one

Product 1

HCID 13576946HCID 13576946, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A cold solution of chlorine in chloroform is added dropwise at from 0° to 5° C., while stirring, to a mixture of 14.7 g (0.063 mole) of 3-methyl-6-morpholinobenzofuran-2(3H)-one in 100 ml of chloroform until no more educt is visible in the thin layer chromatograph. The reaction mixture is diluted with methylene chloride and washed in succession with 10% strength sodium thiosulphate solution, dilute sodium bicarbonate solution and water. The crude product remaining after drying and concentrating by evaporation 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-morpholinobenzofuran-2(3H)-one having a melting point of 103°-105° C.

Workup

  1. washwashed in succession with 10% strength sodium thiosulphate solution, dilute sodium bicarbonate solution and water
  2. customafter drying
  3. concentrationconcentrating by evaporation the organic phase
  4. customis chromatographed over silica gel with petroleum ether/ether
  5. customRecrystallisation of the pure fractions from ether/petroleum ether

Sources & evidence

ORD record
ord-73b0e7ac6a69401bb1a92aeeba9ad1db
Source dataset
uspto-grants-1984_05
Patent number
US04451462

Reaction notes

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