Epichlorohydrin → 2,3-Epoxypropoxy Carbazole

HRID 646648Notes

Reaction equation

HRID 646648 reaction equation
O[C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:15]([CH:17]1[O:19][CH2:18]1)Cl.[OH-:20].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>[O:19]1[CH2:18][CH:17]1[CH2:15][O:20][C:5]1[C:6]2[NH:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]=2[CH:2]=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 1042514-Hydroxycarbazole

Product 1

HCID 866112662,3-Epoxypropoxy CarbazoleYield 64%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

4-Hydroxy carbazole (60 g) obtained in step 1 was charged into a reactor containing water (90 ml). Epichlorohydrin (64.2 g) and tetrabutyl ammonium bromide (6.3 g) were then charged into the reactor under stirring. 50% Sodium hydroxide solution (78 g) was added slowly in 2-3 hours into the reaction mass at about 30° C. After completion of reaction, ethyl acetate (315 ml) and potable water (315 ml) were charged into the reaction mass. The lower aqueous layer was separated and discarded. The ethyl acetate layer was washed with potable water to obtain neutral pH and dried over anhydrous sodium sulphate. The ethyl acetate is distilled out under vacuum below 55° C. to about 100 ml. The reaction mass was chilled to 0-5° C. and filtered and dried at 50-60° C. to give the title compound (50 g) (64%).

Workup

  1. additionwere charged into the reaction mass
  2. customThe lower aqueous layer was separated
  3. washThe ethyl acetate layer was washed with potable water
  4. customto obtain neutral pH
  5. dry with materialdried over anhydrous sodium sulphate
  6. distillationThe ethyl acetate is distilled out under vacuum below 55° C. to about 100 ml
  7. filtrationfiltered
  8. customdried at 50-60° C.

Sources & evidence

ORD record
ord-07b8ec266b8b4422b646eb321f30194d
Source dataset
uspto-grants-2010_04
Patent number
US07705163B2

Reaction notes

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