Sulfuric Acid → HCID 58085709, compound

HRID 1258502Notes

Reaction equation

HRID 1258502 reaction equation
[Br:1][CH2:2][C:3]([C:8]1[CH:9]=[C:10]([N:20]([CH3:22])[CH3:21])[CH:11]=[C:12]([S:14]([F:19])([F:18])([F:17])([F:16])[F:15])[CH:13]=1)(OC)[O:4]C.S(=O)(=O)(O)O>O>[Br:1][CH2:2][C:3]([C:8]1[CH:13]=[C:12]([S:14]([F:19])([F:15])([F:16])([F:17])[F:18])[CH:11]=[C:10]([N:20]([CH3:22])[CH3:21])[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 58085710HCID 58085710, compound

Product 1

HCID 58085709HCID 58085709, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

[3-(2-Bromo-1,1-dimethoxyethyl)-5-pentafluorosulfanylphenyl]dimethylamine (230 mg) was suspended in water (2.3 ml) and then concentrated sulfuric acid (2.3 ml) was added dropwise while cooling. After stirring at RT for 2 h, the mixture was diluted with water (20 ml) and extracted three times with ethyl acetate. The combined organic phases were washed twice with saturated sodium hydrogencarbonate solution, dried over magnesium sulfate, filtered and concentrated. The residue was dissolved in acetonitrile/water, frozen and freeze-dried overnight. 170 mg of the desired compound were obtained.

Workup

  1. temperaturewhile cooling
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic phases were washed twice with saturated sodium hydrogencarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in acetonitrile/water
  8. temperaturefrozen
  9. customfreeze-dried overnight

Sources & evidence

ORD record
ord-c95045c42cb240b99cc03527d31ff561
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

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