Water → 4-Oxiranylmethoxy-9H-carbazole

HRID 1836717Notes

Reaction equation

HRID 1836717 reaction equation
[OH:1][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-].[Na+].O>CS(C)=O>[O:19]1[CH2:18][CH:17]1[CH2:15][O:1][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

Participants

6

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 1042514-Hydroxycarbazole

Product 1

HCID 50207104-Oxiranylmethoxy-9H-carbazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
40 °C

Procedure

10.4 g of 4-hydroxy-carbazole (57 mmol) were dissolved in 31.1 ml of DMSO. 6.9 ml of epichlorohydrin (88 mmol) were added and next 57 ml of a 1 N sodium hydroxide solution. The mixture was stirred for 8 h at 40° C. It was cooled to 20° C. adn 130 ml of water were added. The product was filtered under suction, and washed with 3×30 ml water. The crude material was recrystallized from isopropanol. The substance was dried at 60° C. for 12 h.

Workup

  1. additionwere added
  2. filtrationThe product was filtered under suction
  3. washwashed with 3×30 ml water
  4. customThe crude material was recrystallized from isopropanol
  5. customThe substance was dried at 60° C. for 12 h.

Sources & evidence

ORD record
ord-fc51505abea54b8bacae1871185aa3f7
Source dataset
uspto-grants-2004_08
Patent number
US06777559B2

Reaction notes

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