Hydrochloric Acid → HCID 22381652, compound

HRID 895766Notes

Reaction equation

HRID 895766 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH:23]1[C:36]2[NH:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[S:28][C:27]=2[CH:26]=[CH:25][CH:24]=1.Br[C:38]1[CH:43]=[CH:42][C:41]([CH2:44][CH2:45][CH2:46][CH3:47])=[CH:40][CH:39]=1.CC(C)([O-])C.[Na+].Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH2:44]([C:41]1[CH:42]=[CH:43][C:38]([N:35]2[C:36]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=3[S:28][C:29]3[C:34]2=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:39][CH:40]=1)[CH2:45][CH2:46][CH3:47]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7108PhenothiazineHCID 80271Tri-o-tolylphosphineHCID 5210591-Bromo-4-butylbenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 22381652HCID 22381652, compoundYield 60.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Procedure

A 2 L 3 neck round bottom flask equipped with overhead stirrer, reflux condensor and a nitrogen line was charged with 0.948 g (4.216 mmol) palladium acetate and 2.647 g (8.746 mmol) tri-o-tolylphosphine and 50 ml toluene. The mixture was stirred at ambient temperature for 20 minutes until an orange-red solution was formed. At that time, phenothiazine (19.93 g, 100 mmol), 1-bromo-4-butyl benzene (23.6 g, 110 mmol) and sodium t-butoxide (10.71 g, 100 mmol) along with 1000 mL toluene was added. The reaction was placed in an oil bath and heated to reflux for 15 hours. A sample was taken for HPLC showing that all starting material was gone. A major peak with the retention time of 8.6 minutes was seen. The solution was cooled. 15 mL concentrated HCl was added. The solution was stirred for an additional hour. Then the solution was passed through a neutral alumina column (750 g). The column was rinsed with toluene. The solvent was removed using a rotary evaporator to yield a yellow solid. The solid was recrystallized from toulene/MeOH. 19.6 g of white solid was obtained with 99% purity. The yield was 60.6%. MS: 331. 1H NMR (DMSO) δ0.92 (t, 3H), 1.36 (m, 2H), 1.62 (m, 2H), 2.73 (t, 2H), 6.13 (d, 2H), 6.87(m, 4H), 7.05 (d, 2H), 7.30 (d, 2H), 7.47 (d, 2H).

Workup

  1. temperaturereflux condensor
  2. customwas formed
  3. customThe reaction was placed in an oil bath
  4. temperatureheated
  5. temperatureto reflux for 15 hours
  6. temperatureThe solution was cooled
  7. stirringThe solution was stirred for an additional hour
  8. washThe column was rinsed with toluene
  9. customThe solvent was removed
  10. customa rotary evaporator
  11. customto yield a yellow solid
  12. customThe solid was recrystallized from toulene/MeOH

Sources & evidence

ORD record
ord-356de02e134f45b5b46c63de775c2f9b
Source dataset
uspto-grants-2005_07
Patent number
US06916902B2

Reaction notes

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