Acetic Acid → HCID 19858061, compound

HRID 2073398Notes

Reaction equation

HRID 2073398 reaction equation
Br[CH2:2][C:3]1[CH:15]=[C:14]2[C:6]([CH:7]=[C:8]([S:19]([CH3:22])(=[O:21])=[O:20])[C:9]3[O:10][C:11](=[O:18])[C:12]([CH3:17])([CH3:16])[C:13]=32)=[CH:5][C:4]=1[S:23]([CH3:26])(=[O:25])=[O:24].[NH:27]1[CH:31]=[N:30][CH:29]=[N:28]1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>C(#N)C.O>[S:19]([C:8]1[C:9]2[O:10][C:11](=[O:18])[C:12]([CH3:16])([CH3:17])[C:13]=2[C:14]2[C:6](=[CH:5][C:4]([S:23]([CH3:26])(=[O:24])=[O:25])=[C:3]([CH2:2][N:27]3[CH:31]=[N:30][CH:29]=[N:28]3)[CH:15]=2)[CH:7]=1)([CH3:22])(=[O:20])=[O:21]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 19858047HCID 19858047, compound

Product 1

HCID 19858061HCID 19858061, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 8-bromomethyl-4,7-dimesyl-1,1-dimethyl-2(1H)-naphtho[2,1-b]furanone in acetonitrile (5 ml) was treated with 1,2,4-triazole (0.2 g) and potassium carbonate (0.14 g), and the mixture was stirred under reflux for 18 h. The mixture was diluted with water, neutralised with glacial acetic acid and extracted with ethyl acetate, and the ethyl acetate extract was dried and evaporated to dryness under reduced pressure. The residue was purified by flash chromatography, using methanol:ethyl acetate, 1:99 v/v as eluant, to give 4,7-dimesyl-1,1-dimethyl-8-(1H-1,2,4-triazol-1-ylmethyl)-2(1H)-naphtho[2,1-b]furanone, m.p. 263°-264° after recrystallisation from ethyl acetate.

Workup

  1. temperatureunder reflux for 18 h
  2. extractionextracted with ethyl acetate
  3. extractionthe ethyl acetate extract
  4. customwas dried
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4a01eabf4c114e979cc4eadd2e3674f0
Source dataset
uspto-grants-1990_04
Patent number
US04916148

Reaction notes

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