Hydrochloric Acid → 1-[3-Morpholin-4-yl-5-(pentafluorosulfanyl)phenyl]ethanone

HRID 1258529Notes

Reaction equation

HRID 1258529 reaction equation
CON(C)[C:4](=[O:23])[C:5]1[CH:10]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:8]=[C:7]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:6]=1.[CH3:25][Mg]Br.Cl>C1COCC1.O>[N:17]1([C:7]2[CH:6]=[C:5]([C:4](=[O:23])[CH3:25])[CH:10]=[C:9]([S:11]([F:12])([F:16])([F:15])([F:13])[F:14])[CH:8]=2)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 58136881N-Methoxy-N-methyl-3-morpholin-4-yl-5-(pentafluorosulfanyl)benzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 581367861-[3-Morpholin-4-yl-5-(pentafluorosulfanyl)phenyl]ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-Methoxy-N-methyl-3-morpholin-4-yl-5-(pentafluorosulfanyl)benzamide (2.38 g) was dissolved in THF (50 ml), methylmagnesium bromide (4.22 ml, 3 M in ether) was added dropwise at 0° C. and then the mixture was stirred at RT for 2 h. Then 1N hydrochloric acid (100 ml) was added, and the mixture was diluted with water and extracted by shaking three times with EA. Thereafter, the combined EA phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel (80 g cartridge, n-heptane/EA gradient of 0-70% within 40 min). 1.1 g of the title compound were obtained.

Workup

  1. extractionextracted
  2. stirringby shaking three times with EA
  3. dry with materialThereafter, the combined EA phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customsilica gel (80 g cartridge, n-heptane/EA gradient of 0-70% within 40 min)

Sources & evidence

ORD record
ord-07840875a85f4821a30936a090df6a90
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

Loading…