Dichloromethane → 4-methylsulfonyl-N-[4-chlorophenyl]benzenecarboximidamide

HRID 1166312

反応式

HRID 1166312 の反応式
F[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C[Al](C)C.[CH3:13][S:14]([C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1)(=[O:16])=[O:15].C(Cl)[Cl:26]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:13][S:14]([C:17]1[CH:24]=[CH:23][C:20]([C:21](=[NH:22])[NH:6][C:5]2[CH:7]=[CH:8][C:2]([Cl:26])=[CH:3][CH:4]=2)=[CH:19][CH:18]=1)(=[O:15])=[O:16]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 97314-FluoroanilineHCID 5199814-(Methylsulfonyl)benzonitrileHCID 16682925Trimethylaluminum

生成物 1

HCID 1785047634-methylsulfonyl-N-[4-chlorophenyl]benzenecarboximidamide収率 35%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6212Chloroform溶媒

実験手順

To a suspension of 4-fluoroaniline (4 mL, 40 mmol) in toluene (120 mL), trimethylaluminum (2M solution in toluene, 21 mL, 42 mmol) was added over 15 minutes. The reaction mixture was warmed to room temperature and stirred for 3 hours. A solution of 4-(methylsulfonyl)benzonitrile (7.65 g, 40 mmol) in methylene chloride (100 mL) was added over 10 minutes and the reaction mixture was heated to 70-75° C. After 48 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. The combined filtrates were concentrated in vacuo and the resulting crude intermediate (7.7 g) was purified by chromatography [silica gel, hexane/ethyl acetate, 25/75] to give 4-methylsulfonyl-N-[4-chlorophenyl]benzenecarboximidamide (4.1 g, 35%) as a white solid: mp (DSC) 182° C. Anal. Calc'd. for C14H13N2SO2F: C, 57.52, H, 4.48, N, 9.58, S, 10.97. Found: C, 57.37, H, 4.69, N, 9.21, S, 10.69.

後処理

  1. additionwas added over 15 minutes
  2. temperaturethe reaction mixture was heated to 70-75° C
  3. waitAfter 48 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
  7. concentrationThe combined filtrates were concentrated in vacuo
  8. customthe resulting crude intermediate (7.7 g) was purified by chromatography [silica gel, hexane/ethyl acetate, 25/75]

出典と根拠

ORDレコード
ord-9167eaad106c45a78625ee1e2b690276
出典データセット
uspto-grants-2003_09
特許番号
US06613789B2

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