Ammonia → HCID 178459007、化合物

HRID 225495

反応式

HRID 225495 の反応式
[N+]([O-])(O)=O.[CH2:5]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[NH2:19])[CH:6]=[CH2:7].[N:20]#[C:21][NH2:22].N>C(O)C.O>[CH2:5]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[NH:19][C:21]([NH2:22])=[NH:20])[CH:6]=[CH2:7]

参加物

7

反応物 4

HCID 222AmmoniaHCID 944Nitric Acid2 回HCID 9864Cyanamide2 回HCID 684956872-[(2-Propenyloxy)-methyl]-5-nitrobenzenamine

生成物 1

HCID 178459007HCID 178459007、化合物

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

Nitric acid (1.04 mL of 65%, 15 mmol) is added to a stirred solution of 2-[(2-propenyloxy)-methyl]-5-nitrobenzenamine (3.15 g, 15 mmol) in ethanol (30 mL) at 200C. A solution of cyanamide (0.95 g, 22.5 mmol) in water (1 mL) is then added dropwise to the stirred mixture at 95° C. over a period of 60 min. The mixture is heated at 95° C. for 14 h, with additional aliquots of cyanamide (total 2.2 g, 58 mmol) being added throughout this period and with the acidity being periodically adjusted to pH 3 by the addition of nitric acid (65%). The resulting mixture is cooled to 0° C., basified with aqueous ammonia (5 mL of 25%), diluted with water (150 mL) and extracted with ethyl acetate (3×100 mL). The combined extracts are washed with saturated aqueous ammonium chloride (50 mL), dried (MgSO4), filtered and the solvent is evaporated off under reduced pressure to give the title compound as a brown oil, which is used directly in the next step without further purification.

後処理

  1. additionbeing added throughout this period and with the acidity
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined extracts are washed with saturated aqueous ammonium chloride (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent is evaporated off under reduced pressure

出典と根拠

ORDレコード
ord-e94eaa7fee594f4b821665c3efa7ee49
出典データセット
uspto-grants-2009_07
特許番号
US07557105B2

関連ノート

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