3-(Di-decylaminocarbonyl)-1-nitrobenzene → 3-(Di-decylaminocarbonyl)benzenamine

HRID 1757881노트

반응식

HRID 1757881 반응식
[CH2:1]([N:11]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:12]([C:14]1[CH:15]=[C:16]([N+:20]([O-])=O)[CH:17]=[CH:18][CH:19]=1)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H][H]>[Pd].C(OCC)(=O)C.C1COCC1>[CH2:23]([N:11]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:12]([C:14]1[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=1)=[O:13])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

참가 물질

6

반응물 2

HCID 193889353-(Di-decylaminocarbonyl)-1-nitrobenzeneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 193890183-(Di-decylaminocarbonyl)benzenamine수율 107.2%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To an ice bath cooled solution of 0.80 g (2.69 mmol) of di-decylamine and 0.75 mL (5.4 mmol) of triethylamine in 10 mL of anhydrous methylene chloride was added dropwise a solution of 0.50 g (2.69 mmol) of 3-nitrobenzoyl chloride in 5 mL of methylene chloride with stirring. The mixture was stirred at room temperature for 4 hours. Water was added, the organic layer was separated and dried. The solvent was removed at reduced pressure and the residual oil was purified by chromatography on 30 g of silica gel using 12.5% ethyl acetate-hexane to give 1.0 g of 3-(di-decylaminocarbonyl)-1-nitrobenzene as an oil. The nmr and mass spectra were consistent with the structure. A mixture of 1.0 g of 3-(di-decylaminocarbonyl)-1-nitrobenzene and 0.2 g of 10% palladium on carbon in 20 mL of ethyl acetate and 20 mL of THF was stirred under a hydrogen atmosphere at room temperature for 2 hours when hydrogen uptake ceased. The catalyst was removed by filtration and the filtrate was concentrated to give 1.0 g of 3-(di-decylaminocarbonyl)benzenamine as an oil. The nmr and mass spectra were consistent with the structure.

후처리

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-a22577aed4eb476f934bfcdf2483d33c
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05446189

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