Diethyl Sulfate → HCID 68516392, compound

HRID 1717423Notes

Reaction equation

HRID 1717423 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([OH:17])=[C:15]([C:18]([O:20][CH3:21])=[O:19])[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].S(OCC)(O[CH2:26][CH3:27])(=O)=O>CN(C=O)C>[CH2:26]([O:17][C:16]1[N:12]([C:9]2[CH:8]=[CH:7][C:6]([C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:11][CH:10]=2)[N:13]=[N:14][C:15]=1[C:18]([O:20][CH3:21])=[O:19])[CH3:27]

Participants

4

Reactant 2

HCID 6163Diethyl SulfateHCID 178464872HCID 178464872, compound

Product 1

HCID 68516392HCID 68516392, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 1-{4-[(ethylamino)carbonyl]phenyl}-5-hydroxy-1H-1,2,3-triazole-4-carboxylate (580 mg, 2 mmol) obtained in Example 1211a) and diethyl sulfate (339 mg, 2.2 mmol, 1.1 eq.) in DMF (5 ml) was stirred at 90° C. for 15 hr. The reaction mixture was concentrated to dryness, and chloroform (20 ml) and water (10 ml) were added to the residue. After partitioning, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (hexane/ethyl acetate=1/1 to ethyl acetate/methanol=4/1) to give the title compound as a white powder (210 mg, 33%).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness, and chloroform (20 ml) and water (10 ml)
  2. additionwere added to the residue
  3. customAfter partitioning
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column (hexane/ethyl acetate=1/1 to ethyl acetate/methanol=4/1)

Sources & evidence

ORD record
ord-7758e9854f7b4cd2b028d493826611a1
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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