4-(Methylsulfonyl)aniline → HCID 178425633、化合物

HRID 52312

反応式

HRID 52312 の反応式
[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.[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:20]#[N:21]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:16][C:17]1[CH:18]=[C:19]([C:20](=[NH:21])[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:22]=[CH:23][C:24]=1[CH3:25]

参加物

6

反応物 3

HCID 796174-(Methylsulfonyl)anilineHCID 888943-Chloro-p-toluonitrileHCID 16682925Trimethylaluminum

生成物 1

HCID 178425633HCID 178425633、化合物

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 6212Chloroform溶媒

実験手順

To a suspension of 4-(methylsulfonyl)aniline (2.82 g, 16.5 mmol) in toluene (150 mL), trimethylaluminum (2M solution in toluene, 12.5 mL, 24.7 mmol) was added over 15 minutes. The reaction mixture was warmed to room temperature and stirred for 2.5 hours. A solution of 3-chloro-4-methylbenzonitrile (5 g, 33 mmol) in toluene (100 mL) was added over 10 minutes and the reaction mixture was heated to 90°-95° C. After 20 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/methanol (2/1). The combined filtrates were concentrated in vacuo and the resulting yellowish solid was stirred with a mixture of hexane/ether (2/1, 700 mL). The intermediate was filtered and washed with more of hexane/ether (2/1). The pale yellow solid 3-chloro-4-methyl-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (4.7 g, 88%) was used in the next reaction without further purification: mp (DSC) 179° C. Anal. Calc'd. for C15H15N2SO2Cl: C, 55.81, H, 4.68, N, 8.68. Found: C, 55.65, H, 4.63, N, 8.59.

後処理

  1. additionwas added over 15 minutes
  2. temperaturethe reaction mixture was heated to 90°-95° C
  3. waitAfter 20 hours
  4. temperaturethe reaction mixture was cooled to room temperature
  5. filtrationAfter filtration
  6. washthe residue was washed with a mixture of methylene chloride/methanol (2/1)
  7. concentrationThe combined filtrates were concentrated in vacuo
  8. stirringthe resulting yellowish solid was stirred with a mixture of hexane/ether (2/1, 700 mL)
  9. filtrationThe intermediate was filtered
  10. washwashed with more of hexane/ether (2/1)
  11. customThe pale yellow solid 3-chloro-4-methyl-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (4.7 g, 88%) was used in the next reaction without further purification

出典と根拠

ORDレコード
ord-b3b0a34bbebd4c4f8d05de58db324efd
出典データセット
uspto-grants-1997_04
特許番号
US05616601

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