Ammonium Chloride → HCID 21486679, compound

HRID 1414264Notes

Reaction equation

HRID 1414264 reaction equation
[Mg].Br[CH:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)[CH2:4][CH3:5].[C:14]([C:22]1[CH:39]=[CH:38][C:25]([N:26]([CH2:31][CH2:32][N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])[S:27]([CH3:30])(=[O:29])=[O:28])=[CH:24][CH:23]=1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>O1CCCC1.O>[CH2:36]([N:33]([CH2:34][CH3:35])[CH2:32][CH2:31][N:26]([S:27]([CH3:30])(=[O:28])=[O:29])[C:25]1[CH:38]=[CH:39][C:22]([C:14]([OH:21])([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:3]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[CH2:4][CH3:5])=[CH:23][CH:24]=1)[CH3:37]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 5462224Magnesium3×HCID 125777181-(1-Bromopropyl)-4-methoxybenzene3×HCID 21486663HCID 21486663, compound

Product 1

HCID 21486679HCID 21486679, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent3×

Procedure

Magnesium turnings (10.0 g., 0.411 mole) are employed to prepare the Grignard reagent from 0.333 mole of p-(1-bromopropyl)anisole in 500 ml. of tetrahydrofuran which has been previously dried by distillation for lithium aluminum hydride. The Grignard reaction is initiated by adding a small portion of the p-(1-bromopropyl)anisole to a small portion of the magnesium turnings in a beaker and when the reaction commences as evidenced by a rise in temperature of the mixture it is transferred to the main reaction flask containing the remaining magnesium turnings and tetrahydrofuran solvent. A nitrogen atmosphere is maintained over the reaction mixture which is cooled at 0°-5°C. The main portion of the p-(1-bromopropyl)anisole dissolved in 700 ml. of similarly dried tetrahydrofuran is then added dropwise to the reaction flask during a period of 30 min. The mixture is then agitated overnight (16 hr.) with cooling and then employed for reaction in the same flask with the substituted benzoylmethanesulfonanilide reactant. 4'-Benzoyl-N-(2-diethylaminoethyl)methanesulfonanilide (25.0 g., 0.0667 mole) dissolved in 200 ml. of dried tetrahydrofuran is added dropwise during 45 min. to the reaction mixture with cooling and stirring which is continued for 24 hr. after the material has been added. The reaction product is then recovered by removing the excess magnesium by filtration and treatment of the filtrate first with water (18.0 g., 1.00 mole) and then with a solution of 50 g. of ammonium chloride in 500 ml. of water. Stirring is continued for 1/2 hr. and the organic layer is then separated and concentrated under reduced pressure. The residual oil is dissolved in ether, the solution washed first with water, the with saturated sodium chloride, and dried over magnesium sulfate. Excess hydrogen chloride gas is then introduced into the solution with stirring and the precipitated hydrochloride salt is collected on a filter and washed with ether; yield 35.2 g. (66%), m.p. 75°-140°C.

Workup

  1. dry with materialof tetrahydrofuran which has been previously dried by distillation for lithium aluminum hydride
  2. customThe Grignard reaction
  3. customthe reaction commences
  4. temperatureA nitrogen atmosphere is maintained over the reaction mixture which
  5. temperatureis cooled at 0°-5°C
  6. temperaturewith cooling
  7. temperaturewith cooling
  8. stirringstirring which
  9. waitis continued for 24 hr
  10. additionafter the material has been added
  11. customThe reaction product is then recovered
  12. customby removing the excess magnesium
  13. stirringStirring
  14. waitis continued for 1/2 hr
  15. customand the organic layer is then separated
  16. concentrationconcentrated under reduced pressure
  17. dissolutionThe residual oil is dissolved in ether
  18. washthe solution washed first with water
  19. dry with materialthe with saturated sodium chloride, and dried over magnesium sulfate
  20. additionExcess hydrogen chloride gas is then introduced into the solution
  21. stirringwith stirring
  22. customthe precipitated hydrochloride salt is collected on
  23. filtrationa filter
  24. washwashed with ether

Sources & evidence

ORD record
ord-06125205c9aa451e8136c79c5b786d82
Source dataset
uspto-grants-1977_01
Patent number
US04001229

Reaction notes

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