4-(Methylsulfonyl)aniline → HCID 178491240、化合物

HRID 52316

反応式

HRID 52316 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.[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[C:20]#[N:21]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[F: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[O:25][CH3:26]

参加物

6

反応物 3

HCID 796174-(Methylsulfonyl)anilineHCID 27745483-Fluoro-4-methoxybenzonitrileHCID 16682925Trimethylaluminum

生成物 1

HCID 178491240HCID 178491240、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-fluoro-4-methoxybenzonitrile (5 g, 33 mmol) in toluene (100 mL) was added over 10 minutes and the reaction mixture was heated to 80°-85° 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 reside 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, 1000 mL). The intermediate was filtered and washed with more hexane/ether (2/1). The pale yellow solid 3-fluoro-4-methoxy-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (3.95 g, 74%) was used in the next reaction without further purification: mp (DSC) 195° C. Anal. Calc'd. for C15H15N2SO3F: C, 55.89, H, 4.69, N, 8.69. Found: C, 55.92, H, 4.74, N, 8.53.

後処理

  1. additionwas added over 15 minutes
  2. temperaturethe reaction mixture was heated to 80°-85° C
  3. waitAfter 20 hours
  4. temperaturethe reaction mixture was cooled to room temperature
  5. filtrationAfter filtration
  6. washthe reside 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, 1000 mL)
  9. filtrationThe intermediate was filtered
  10. washwashed with more hexane/ether (2/1)
  11. customThe pale yellow solid 3-fluoro-4-methoxy-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (3.95 g, 74%) was used in the next reaction without further purification

出典と根拠

ORDレコード
ord-4f3accbe569b48688531b22fb862f88a
出典データセット
uspto-grants-1997_04
特許番号
US05616601

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