4-(Methylsulfonyl)aniline hydrochloride → HCID 178491241, compound

HRID 1352984Notes

Reaction equation

HRID 1352984 reaction equation
Cl.[CH3:2][S:3]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)(=[O:5])=[O:4].C[Al](C)C.[CH3:17][O:18][C:19]1[N:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([C:25](=[NH:26])[NH:10][C:9]2[CH:11]=[CH:12][C:6]([S:3]([CH3:2])(=[O:4])=[O:5])=[CH:7][CH:8]=2)=[CH:23][N:24]=1

Participants

6

Reactant 3

HCID 27351804-(Methylsulfonyl)aniline hydrochlorideHCID 27367762-Methoxy-5-pyridinecarbonitrileHCID 16682925Trimethylaluminum

Product 1

HCID 178491241HCID 178491241, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6212ChloroformSolvent

Procedure

To a suspension of 4-(methylsulfonyl)aniline hydrochloride (1.8 g, 8.7 mmol) in toluene (50 ml) at 0° C., trimethylaluminum (2M solution in toluene, 5.2 ml, 10.4 mmol) was added over 10 minutes. The reaction mixture was warmed to room temperature and stirred for 2 hours. A solution of 6-methoxy-3-cyanopyridine (1.75 g, 13 mmol) in toluene (100 ml) was added over 10 minutes and the mixture was heated to 85–90° C. After 24 hours, the reaction mixture was cooled to room temperature and poured over a slurry of silica gel in chloroform. After filtration, the residue was washed with a mixture of methylene chloride and methanol and later with methanol. The combined filtrates were concentrated and the resulting yellowish solid was stirred with ethyl acetate (1000 ml) and filtered. The white solid (2 g, 75%) was used in the next reaction without further purification. Anal. Calc'd. for C14H16N3SClO3.0.5H2O: C, 47.93; H, 4.88; N, 11.98. Found: C, 48.01; H, 4.82; N, 11.32.

Workup

  1. temperaturethe mixture was heated to 85–90° C
  2. waitAfter 24 hours
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationAfter filtration
  5. washthe residue was washed with a mixture of methylene chloride and methanol and later with methanol
  6. concentrationThe combined filtrates were concentrated
  7. stirringthe resulting yellowish solid was stirred with ethyl acetate (1000 ml)
  8. filtrationfiltered
  9. customThe white solid (2 g, 75%) was used in the next reaction without further purification

Sources & evidence

ORD record
ord-322c98769910409c9c681954676a3dfb
Source dataset
uspto-grants-2007_05
Patent number
US07220770B2

Reaction notes

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