Propoxur → 2-Isopropoxyphenyl [[(diethoxyphosphinothioyl)anilino]thio]methylcarbamate

HRID 1706708

反応式

HRID 1706708 の反応式
Cl[S:2][N:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[P:4](=[S:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7].[CH3:18][NH:19][C:20](=[O:32])[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH:29]([CH3:31])[CH3:30].CN(C)C=O>C(OCC)C.O>[CH2:6]([O:5][P:4]([N:3]([S:2][CH2:18][NH:19][C:20](=[O:32])[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH:29]([CH3:30])[CH3:31])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:8][CH2:9][CH3:10])=[S:11])[CH3:7]

参加物

6

反応物 3

HCID 4944PropoxurHCID 6228DimethylformamideHCID 54509702O,O-diethyl N-(chlorothio)phenylphosphoramidothioate

生成物 1

HCID 203412672-Isopropoxyphenyl [[(diethoxyphosphinothioyl)anilino]thio]methylcarbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

The O,O-diethyl N-(chlorothio)phenylphosphoramidothioate as a yellow oil obtained in Part A, above, is dissolved in a minimal amount of diethyl ether (about 5 ml) and the ether solution is added to a cooled (0° C.) solution consisting of 6.34 gm (0.030 mole) of 2-isopropoxyphenyl methylcarbamate and 20 ml dimethylformamide. This reaction mixture is stirred as it is permitted to warm to 25° C., and stirring is continued for four hours. The mixture is then diluted with 100 ml water and extracted with diethyl ether. The ether phase is recovered, washed with water, and dried over anhydrous sodium sulfate. The ether is removed by evaporation under reduced pressure. The oily residue thus obtained is chromatographed through a column of silica gel. Development is with methylene chloride. After removing the methylene chloride by evaporation under reduced pressure, there is obtained 1.02 gm. of the crude product as an amber oil which is crystallized from petroleum ether having a boiling range between 30° and 60° C. to give 2-isopropoxyphenyl [[(diethoxyphosphinothioyl)anilino]thio]methylcarbamate as colorless crystals having a melting point at 69° to 70.5° C.

後処理

  1. temperatureto warm to 25° C.
  2. stirringstirring
  3. extractionextracted with diethyl ether
  4. customThe ether phase is recovered
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe ether is removed by evaporation under reduced pressure
  8. customThe oily residue thus obtained
  9. customis chromatographed through a column of silica gel
  10. customAfter removing the methylene chloride
  11. customby evaporation under reduced pressure
  12. customthere is obtained 1.02 gm
  13. customof the crude product as an amber oil which is crystallized from petroleum ether having a boiling range between 30° and 60° C.

出典と根拠

ORDレコード
ord-4f29e5e05eff4e3fa292484e506433ac
出典データセット
uspto-grants-1980_06
特許番号
US04208409

関連ノート

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