4-(Methylsulfonyl)aniline → HCID 178504793, compound

HRID 2086647Notes

Reaction equation

HRID 2086647 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.[C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[CH:20][CH:19]=1)#[N:17]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.CO>[CH3:1][S:2]([C:5]1[CH:11]=[CH:10][C:8]([NH:9][C:16]([C:18]2[CH:19]=[CH:20][C:21]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)=[CH:22][CH:23]=2)=[NH:17])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

6

Reactant 3

HCID 796174-(Methylsulfonyl)anilineHCID 35641934-(2-thienyl)benzonitrileHCID 16682925Trimethylaluminum

Product 1

HCID 178504793HCID 178504793, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 21584188Chloroform methanolSolvent

Procedure

To a suspension of 4-(methylsulfonyl)aniline (0.428 g, 2.5 mmol) in toluene (15 mL) at 0° C. was added over 5 minutes trimethylaluminum (3.83 mL, 0.98 M solution in hexane, 3.75 mmol). The reaction mixture was warmed to room temperature and stirred for 3.5 hours. A solution of 2-(4-cyanophenyl)thiophene (0.926 g, 5 mmol, prepared according to the method of Heterocycles, 1990, 31, 1951) in toluene (10 mL) was added over 5 minutes and the reaction mixture heated to 70° C. After 18.5 hours, the reaction mixture was cooled to room temperature and poured over a slurry of silicagel in chloroform-methanol (2:1, 150 mL). After filtration, the residue was washed with a mixture of CH2Cl2-methanol (2:1, 75 mL). The combined filtrates were concentrated in vacuo, and the resulting yellowish solid was washed with hexane-ether (2:1, 100 mL) to give the subtitle compound (0.711 g).

Workup

  1. additionwas added over 5 minutes
  2. temperaturethe reaction mixture heated to 70° C
  3. waitAfter 18.5 hours
  4. temperaturethe reaction mixture was cooled to room temperature
  5. filtrationAfter filtration
  6. washthe residue was washed with a mixture of CH2Cl2-methanol (2:1, 75 mL)
  7. concentrationThe combined filtrates were concentrated in vacuo
  8. washthe resulting yellowish solid was washed with hexane-ether (2:1, 100 mL)

Sources & evidence

ORD record
ord-967a7b1085a449cd922f05b4e4fb45fc
Source dataset
uspto-grants-2004_04
Patent number
US06727238B2

Reaction notes

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