Toluene → Diphenylamine

HRID 1155501Notes

Reaction equation

HRID 1155501 reaction equation
C1(C)C=CC=CC=1.S(Cl)Cl.[Na].[C:12]1([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[C:19]1([NH:18][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 25353Sulfur dichlorideHCID 53445856HCID 53445856, compound

Product 1

HCID 11487Diphenylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The toluene solution of the sulfenyl chloride was added to the THF solution of the diphenylamine sodium salt. The reaction mixture was stirred cold for 1 hour, cooling was removed and the reaction was stirred an additional hour. The reaction mixture was filtered through celite and solvent was removed in vacuum leaving a brown oil. Chromatography on silica gel yielded the desired product as a yellow oil which solidified on trituration with hexanes (m 109°-122° C.).

Workup

  1. temperaturecooling
  2. customwas removed
  3. stirringthe reaction was stirred an additional hour
  4. filtrationThe reaction mixture was filtered through celite and solvent
  5. customwas removed in vacuum
  6. customleaving a brown oil

Sources & evidence

ORD record
ord-1ce61c0652724a2e9d081d39f3142785
Source dataset
uspto-grants-1981_11
Patent number
US04302451

Reaction notes

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