Ethyl Acetate → HCID 19432961, compound

HRID 1736419Notes

Reaction equation

HRID 1736419 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:12]([C:14]2[CH:15]=[CH:16][C:17]([S:20][CH3:21])=[N:18][CH:19]=2)=[CH2:13])[CH2:11][O:10]1.C(=O)([O-])[O-].[K+].[K+].[NH:28]1[CH:32]=[N:31][CH:30]=[N:29]1.C(OCC)(=O)C>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:10])([C:12]([C:14]1[CH:15]=[CH:16][C:17]([S:20][CH3:21])=[N:18][CH:19]=1)=[CH2:13])[CH2:11][N:28]1[CH:32]=[N:31][CH:30]=[N:29]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 19432959HCID 19432959, compound

Product 1

HCID 19432961HCID 19432961, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of the product of part (vi) (3.6 g, 13 mmol) in DMF (30 ml) was added to potassium carbonate (2.0 g, 15 mmol) and 1H-1,2,4-triazole (1.0 g, 15 mmol). The mixture was stirred at 50° C. for 20 hours then poured into ethyl acetate (200 ml) and washed with water (2×100 ml). The organic phase was dried (MgSO4) and evaporated under reduced pressure. Flash chromatography of the residue on silica by elution with ethyl acetate gave the title compound as an oil, (3.5 g).

Workup

  1. washwashed with water (2×100 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated under reduced pressure
  4. washFlash chromatography of the residue on silica by elution with ethyl acetate

Sources & evidence

ORD record
ord-bc084ad092874c3a96b668c50268fb83
Source dataset
uspto-grants-1996_07
Patent number
US05541203

Reaction notes

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