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

HRID 1110319

反応式

HRID 1110319 の反応式
[CH2:1]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(N(CC)CC)C.[N+:29]([C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](Cl)=[O:36])([O-:31])=[O:30].O>C(Cl)Cl>[CH2:12]([N:11]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:35]([C:34]1[CH:33]=[C:32]([N+:29]([O-:31])=[O:30])[CH:40]=[CH:39][CH:38]=1)=[O:36])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 14261Didecylamine

生成物 1

HCID 193889353-(Di-decylaminocarbonyl)-1-nitrobenzene収率 83.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. customthe organic layer was separated
  3. customdried
  4. customThe solvent was removed at reduced pressure
  5. customthe residual oil was purified by chromatography on 30 g of silica gel using 12.5% ethyl acetate-hexane

出典と根拠

ORDレコード
ord-cd075d6c55d54adc908460f0d35d2829
出典データセット
uspto-grants-1994_06
特許番号
US05324747

関連ノート

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