Sulfuric Acid → Diethyl (4-chloro-2-nitroanilino)methylphosphonate

HRID 343987

反応式

HRID 343987 の反応式
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH2:12]([O:14][P:15]([O-:19])[O:16][CH2:17][CH3:18])[CH3:13].S(=O)(=O)(O)O.[CH2:25](OCOCC)C>O>[CH2:12]([O:14][P:15]([CH2:25][NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10])(=[O:19])[O:16][CH2:17][CH3:18])[CH3:13]

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 69794-Chloro-2-nitroanilineHCID 10024Diethoxymethane2 回HCID 3780918Diethylphosphite

生成物 1

HCID 603785Diethyl (4-chloro-2-nitroanilino)methylphosphonate収率 95%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
95 °C

実験手順

With stirring and under a nitrogen atmosphere 4-chloro-2-nitroaniline (5 g, 28.9 mmole) was dissolved in diethylphosphite (21.44 g, 155 mmole), followed by the addition of a solution of sulfuric acid (0.1 mL) and water (0.1 mL). Under a continuous flow of nitrogen the solution was heated to 95° C., after which diethoxymethane (9.05 g, 86.8 mmole) was added in a dropwise manner over a period of 1.5 hours while maintaining the temperature between 93°-97° C. Once all the diethoxymethane was added, the reaction was kept at 95°-105° C. for another hour after which the mixture was cooled to 45°-50° C. and cold water (70 mL) was added over 20 minutes. The resulting suspension was filtered, washed first with water (10 mL), then with heptane (10 mL). The obtained orange solid was dried at 30°-40° C. for 16 hours to yield 8.85 g (95%) of the title compound, mp 94°-5° C.

後処理

  1. temperaturewhile maintaining the temperature between 93°-97° C
  2. waitthe reaction was kept at 95°-105° C. for another hour
  3. temperatureafter which the mixture was cooled to 45°-50° C.
  4. filtrationThe resulting suspension was filtered
  5. washwashed first with water (10 mL)
  6. customThe obtained orange solid was dried at 30°-40° C. for 16 hours

出典と根拠

ORDレコード
ord-aae98600148745eb81ca288f533f5fc3
出典データセット
uspto-grants-1999_01
特許番号
US05864040

関連ノート

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