Epichlorohydrin → HCID 13787418, compound

HRID 1165217Notes

Reaction equation

HRID 1165217 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:12]2[CH:13]=[CH:14][NH:15][C:16]=2[CH:17]=[CH:18][CH:19]=1)=[O:10].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:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:12]2[CH:13]=[CH:14][NH:15][C:16]=2[CH:17]=[CH:18][CH:19]=1)=[O:10]

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 13787417HCID 13787417, compound

Product 1

HCID 13787418HCID 13787418, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under an inert atmosphere, a solution of 3 g of N-(2-hydroxyphenyl)-1H-indol-4-carboxamide and 1.65 g of potassium carbonate in 100 ml of acetone was refluxed for 24 hours with 4.7 ml of epichlorhydrin and after purifying by chromatography over silica (eluent: ethyl acetate-triethylamine, 9-1) and evaporating to dryness, the residue was triturated in pentane, then filtered and dried under reduced pressure at 60° C. to obtain 2.8 g of N-[2-[(2-oxiranyl)methoxy]phenyl]-1H-indol-4-carboxamide melting at 122° C.

Workup

  1. customafter purifying by chromatography over silica (eluent: ethyl acetate-triethylamine, 9-1)
  2. customevaporating to dryness
  3. customthe residue was triturated in pentane
  4. filtrationfiltered
  5. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-7f9d819e15ab48a6a443036ef0ce97c4
Source dataset
uspto-grants-1990_03
Patent number
US04908367

Reaction notes

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