Sodium Sulfide → 3-Methoxy-5-nitroaniline

HRID 420360ノート

反応式

HRID 420360 の反応式
C(=O)(O)[O-].[Na+].[S-2].[Na+].[Na+].[N+:9]([C:12]1[CH:13]=[C:14]([O:21][CH3:22])[CH:15]=[C:16]([N+:18]([O-])=O)[CH:17]=1)([O-:11])=[O:10]>O.CO>[CH3:22][O:21][C:14]1[CH:15]=[C:16]([NH2:18])[CH:17]=[C:12]([N+:9]([O-:11])=[O:10])[CH:13]=1

参加物

6

反応物 3

HCID 14804Sodium SulfideHCID 79231Benzene, 1-methoxy-3,5-dinitro-HCID 516892Sodium Bicarbonate2 回

生成物 1

HCID 27595983-Methoxy-5-nitroaniline収率 93.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

Sodium bicarbonate (5.62 g, 66.87 mmol) was added to a solution of sodium sulfide (5.5 g, 70.58 mmol) in deionized water (60 mL). When the sodium bicarbonate was completely dissolved, methanol (50 mL) was added, and the solution was cooled to 0° C. A precipitate formed, which was removed by filtration through a Celite pad. The filtered solution was added quickly to a solution of 3,5-dinitroanisole (7.36 g, 37.15 mmol) in methanol (50 mL). The resulting suspension was heated to reflux for 30 min and then the solution was concentrated in vacuo to remove methanol. The aqueous residue was poured into 200 mL of ice-water, and the resulting orange precipitate was collected by filtration. After air-drying, 3-methoxy-5-nitro-phenylamine (5.82 g, 93%) was obtained as light brown solid: ES(+)-HRMS m/e calculated for C7H8N2O3 (M+H)+ 169.0608, found 169.0608.

後処理

  1. customA precipitate formed
  2. customwhich was removed by filtration through a Celite pad
  3. temperatureThe resulting suspension was heated
  4. temperatureto reflux for 30 min
  5. concentrationthe solution was concentrated in vacuo
  6. customto remove methanol
  7. additionThe aqueous residue was poured into 200 mL of ice-water
  8. filtrationthe resulting orange precipitate was collected by filtration
  9. customAfter air-drying

出典と根拠

ORDレコード
ord-355cf9e651c1456586160eaca41743e6
出典データセット
uspto-grants-2012_01
特許番号
US08093385B2

反応ノート

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