Epichlorohydrin → HCID 15611138, compound

HRID 1768986Notes

Reaction equation

HRID 1768986 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:26]([CH:28]1[O:30][CH2:29]1)Cl>CC(C)=O>[O:30]1[CH2:29][CH:28]1[CH2:26][O:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)=[O:5]

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 13787428HCID 13787428, compound

Product 1

HCID 15611138HCID 15611138, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3.5 g of 2-hydroxy-N-(1H-indol-4-yl)benzamide and 1.9 g of potassium carbonate in 100 ml of acetone was refluxed for 30 hours under an inert atmosphere with 11 ml of epichlorohydrin and the insoluble material was filtered off. The filtrate was evaporated to dryness and the residue was purified by chromatography over silica (eluent:chloroform/acetone/TEA 6:3:1). Fractions having a Rf=0.45 were evaporated to dryness and the residue was empasted with ether, filtered and dried under reduced pressure at 60° C. to obtain 3.65 g of 2-[(2-oxiranyl)methoxy]-N-(1H-indol-4-yl)benzamide melting at 171° C.

Workup

  1. filtrationthe insoluble material was filtered off
  2. customThe filtrate was evaporated to dryness
  3. customthe residue was purified by chromatography over silica (eluent:chloroform/acetone/TEA 6:3:1)
  4. customwere evaporated to dryness
  5. filtrationfiltered
  6. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-9fe6c4338a634f12876f13b9ecdf8088
Source dataset
uspto-grants-1995_01
Patent number
US05380722

Reaction notes

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