Methyl sulfate(1-) → HCID 86747305, compound

HRID 1656340Notes

Reaction equation

HRID 1656340 reaction equation
S([O-])(O[CH3:5])(=O)=O.[F:7][C:8]([C:11]1[C:12](=[O:25])[C:13]([OH:24])=[N:14][N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]=1[CH3:17])([F:10])[F:9]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.CCOCC>[F:9][C:8]([C:11]1[C:12](=[O:25])[C:13]([O:24][CH3:5])=[N:14][N:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:16]=1[CH3:17])([F:7])[F:10]

Participants

6

Reactant 2

HCID 4694097Methyl sulfate(1-)HCID 178427868HCID 178427868, compound

Product 1

HCID 86747305HCID 86747305, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Tetrabutylammonium bromide (635 mg), 6N soda (13 ml), and methyl sulfate (5.59 ml) are added to a solution of Compound 1 (5.31 grams) in THF. After 1 hour 30 minutes of stirring at 25° C., the solution is evaporated under vacuum, dissolved in water, and extracted with ethyl acetate. After washing with water, drying, filtration and evaporation under vacuum, a residue is obtained which is dissolved in ether and recrystallized from a 60/40 mixture of dioxane and hexane, to provide Compound 2 (3.97 grams; yield 71%).

Workup

  1. customthe solution is evaporated under vacuum
  2. dissolutiondissolved in water
  3. extractionextracted with ethyl acetate
  4. washAfter washing with water
  5. customdrying
  6. filtrationfiltration and evaporation under vacuum
  7. customa residue is obtained which
  8. customrecrystallized from a 60/40 mixture of dioxane and hexane

Sources & evidence

ORD record
ord-1515374e4e1143ef8063edec5347b130
Source dataset
uspto-grants-1993_10
Patent number
US05254554

Reaction notes

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