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

HRID 343987

반응식

HRID 343987 반응식
[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]

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 69794-Chloro-2-nitroanilineHCID 10024Diethoxymethane2회HCID 3780918Diethylphosphite

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
95 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aae98600148745eb81ca288f533f5fc3
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05864040

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