Water → HCID 54516723, compound

HRID 2073386Notes

Reaction equation

HRID 2073386 reaction equation
Br[CH2:2][C:3]1[CH:15]=[C:14]2[C:6]([CH:7]=[CH:8][C:9]3[O:10][C:11](=[O:18])[C:12]([CH3:17])([CH3:16])[C:13]=32)=[CH:5][C:4]=1[C:19]#[N:20].[NH:21]1[CH:25]=[N:24][CH:23]=[N:22]1.[Na].O>CN(C)C=O>[CH3:16][C:12]1([CH3:17])[C:11](=[O:18])[O:10][C:9]2[CH:8]=[CH:7][C:6]3[C:14]([C:13]1=2)=[CH:15][C:3]([CH2:2][N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)=[C:4]([C:19]#[N:20])[CH:5]=3

Participants

5

Reactant 3

HCID 962WaterHCID 19858052HCID 19858052, compoundHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 54516723HCID 54516723, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 8-bromomethyl-1,2-dihydro-1,1-dimethyl-2-oxonaphtho[2,1-b]furan-7-carbonitrile in N,N-dimethylformamide (3 ml) was treated with sodium 1,2,4-triazole (0.18 g) and the mixture was stirred at room temperature for 4 h, then treated with water (20 ml). The mixture was extracted twice with ethyl acetate and the combined extracts were 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 1,2-dihydro-1,1-dimethyl-2-oxo-8-(1H-1,2,4-triazol-1-ylmethyl)naphtho(2,1-b)-furan-7-carbonitrile, m.p. 198°-198° after recrystallisation from a mixture of ethyl acetate and cyclohexane.

Workup

  1. extractionThe mixture was extracted twice with ethyl acetate
  2. customthe combined extracts were dried
  3. customevaporated to dryness under reduced pressure
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0ba36d953b764eb2a1c30c098a990ba3
Source dataset
uspto-grants-1990_04
Patent number
US04916148

Reaction notes

Loading…