Triethylamine → Bis(4-tert-butoxyphenyl)(4-dimethylaminophenyl)sul fonium p-toluenesulfonate

HRID 1457422Notes

Reaction equation

HRID 1457422 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:16][CH:15]=2)=O)=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C[Si]([O:36][S:37]([C:40]1[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=1)(=[O:39])=[O:38])(C)C.Br[C:48]1[CH:56]=[CH:55][C:51]([N:52]([CH3:54])[CH3:53])=[CH:50][CH:49]=1.[Mg].[Cl-].[NH4+]>C(Cl)Cl.C1COCC1>[C:43]1([CH3:46])[CH:42]=[CH:41][C:40]([S:37]([O-:39])(=[O:36])=[O:38])=[CH:45][CH:44]=1.[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S+:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:16][CH:15]=2)[C:48]2[CH:56]=[CH:55][C:51]([N:52]([CH3:54])[CH3:53])=[CH:50][CH:49]=2)=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 114654-bromo-N,N-dimethylanilineHCID 25517Ammonium ChlorideHCID 615236Silanol, trimethyl-, 4-methylbenzenesulfonateHCID 5462224MagnesiumHCID 15389810Bis(4-tert-butoxyphenyl) sulfoxide

Product 1

HCID 22290296Bis(4-tert-butoxyphenyl)(4-dimethylaminophenyl)sul fonium p-toluenesulfonateYield 49%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8.5 grams (0.025 mol) of bis(4-tert-butoxyphenyl) sulfoxide in 300 grams of methylene chloride was cooled in an ice water bath. To the solution, 1.3 grams (0.013 mol) of triethylamine was added and 12.2 grams (0.05 mol) of trimethylsilyl-p-toluenesulfonate was added dropwise in a controlled manner so that the temperature might not exceed 10° C. The reaction solution was ripened for 30 minutes while maintaining a reaction temperature of 0° to 10° C. A Grignard reagent, which was separately prepared in a conventional manner using 10.0 grams (0.05 mol) of 4-bromo-N,N-dimethylaniline, 1.2 grams (0.05 mol) of magnesium and 50 grams of THF, was added dropwise to the reaction solution in a controlled manner so that the temperature might not exceed 10° C. The reaction solution was ripened for 30 minutes while maintaining a reaction temperature of 0° to 10° C. 200 grams of an aqueous solution of 20% ammonium chloride was added to the reaction solution to terminate reaction. After separation, 200 grams of chloroform was added to the organic layer. After the organic layer was washed twice with 200 grams of water, the solvent was distilled off in vacuum, yielding an oily residue. The oily residue was recrystallized, isolating 7.6 grams (yield 49%) of bis(4-tert-butoxyphenyl)(4-dimethylaminophenyl)sul fonium p-toluenesulfonate with 99% purity.

Workup

  1. customexceed 10° C
  2. temperaturewhile maintaining a reaction temperature of 0° to 10° C
  3. additionwas added dropwise to the reaction solution in a controlled manner so that the temperature might not
  4. customexceed 10° C
  5. waitThe reaction solution was ripened for 30 minutes
  6. temperaturewhile maintaining a reaction temperature of 0° to 10° C
  7. customto terminate
  8. customreaction
  9. customAfter separation, 200 grams of chloroform
  10. additionwas added to the organic layer
  11. washAfter the organic layer was washed twice with 200 grams of water
  12. distillationthe solvent was distilled off in vacuum
  13. customyielding an oily residue
  14. customThe oily residue was recrystallized

Sources & evidence

ORD record
ord-6a904b7894fa4ddf9fcd558bc89cebb4
Source dataset
uspto-grants-1998_12
Patent number
US05847218

Reaction notes

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