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

HRID 52297

반응식

HRID 52297 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 1785047634-methylsulfonyl-N-[4-chlorophenyl]benzenecarboximidamide수율 35%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6212Chloroform용매

실험 절차

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 chromatographed [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.

후처리

  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 chromatographed [silica gel, hexane/ethyl acetate, 25/75]

출처 및 근거

ORD 기록
ord-79d9344789514a02b4037e46ddef742f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616601

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