p-Tolunitrile → HCID 178425632, compound

HRID 52331

Reaction equation

HRID 52331 reaction equation
[CH3:1][S:2]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C[Al](C)C.[CH3:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:16][C:17]1[CH:24]=[CH:23][C:20]([C:21](=[NH:22])[NH:9][C:8]2[CH:10]=[CH:11][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7724p-TolunitrileHCID 796174-(Methylsulfonyl)anilineHCID 16682925Trimethylaluminum

Product 1

HCID 178425632HCID 178425632, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6212ChloroformSolvent

Procedure

To a suspension of 4-(methylsulfonyl)aniline (10 mmol) in toluene (100 mL), trimethylaluminum (2M solution in toluene, 15 mmol) is added over 15 minutes. The reaction mixture is warmed to room temperature and stirred for 2.5 hours. A solution of 4-methylbenzonitrile (20 mmol) in toluene (50 mL) is added over 10 minutes and the reaction mixture is heated to 80°-85° C. After 20 hours, the reaction mixture is cooled to room temperature and poured over a slurry of silica gel in chloroform. After filtration, the residue is washed with a mixture of methylene chloride/methanol (2/1). The combined filtrates are concentrated in vacuo and the resulting yellowish solid is stirred with a mixture of hexane/ether (2/1, 1000 mL). The intermediate is filtered and washed with more of hexane/ether (2/1). The pale yellow solid 4-methyl-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide is used in the next reaction without further purification.

Workup

  1. additionis added over 15 minutes
  2. temperaturethe reaction mixture is heated to 80°-85° C
  3. waitAfter 20 hours
  4. temperaturethe reaction mixture is cooled to room temperature
  5. filtrationAfter filtration
  6. washthe residue is washed with a mixture of methylene chloride/methanol (2/1)
  7. concentrationThe combined filtrates are concentrated in vacuo
  8. stirringthe resulting yellowish solid is stirred with a mixture of hexane/ether (2/1, 1000 mL)
  9. filtrationThe intermediate is filtered
  10. washwashed with more of hexane/ether (2/1)
  11. customThe pale yellow solid 4-methyl-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide is used in the next reaction without further purification

Sources & evidence

ORD record
ord-90a83a5105b5410da8c84b5f013cffeb
Source dataset
uspto-grants-1997_04
Patent number
US05616601

Linked notes

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