Diethyl Ether → 4-(Dimethylamino)-3,5-xylyl [[(diethoxyphosphinothioyl)-n-propylamino]thio]methylcarbamate

HRID 1706707Notes

Reaction equation

HRID 1706707 reaction equation
Cl[S:2][N:3]([CH2:12][CH2:13][CH3:14])[P:4](=[S:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7].[CH3:15][NH:16][C:17](=[O:30])[O:18][C:19]1[CH:24]=[C:23]([CH3:25])[C:22]([N:26]([CH3:28])[CH3:27])=[C:21]([CH3:29])[CH:20]=1.[O-][Si]([O-])=O.[Mg+2].C(OCC)C>CN(C)C=O.CCCCCC>[CH2:6]([O:5][P:4]([N:3]([CH2:12][CH2:13][CH3:14])[S:2][CH2:15][NH:16][C:17](=[O:30])[O:18][C:19]1[CH:24]=[C:23]([CH3:25])[C:22]([N:26]([CH3:27])[CH3:28])=[C:21]([CH3:29])[CH:20]=1)([O:8][CH2:9][CH3:10])=[S:11])[CH3:7]

Participants

7

Reactant 4

HCID 3283Diethyl Ether2×HCID 9414MexacarbateHCID 61680MAGNESIUM SILICATE (synthetic)HCID 20333951O,O-diethyl N-(chlorothio)-n-propylphosphoramidothioate

Product 1

HCID 867370564-(Dimethylamino)-3,5-xylyl [[(diethoxyphosphinothioyl)-n-propylamino]thio]methylcarbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
25 °C

Procedure

The crude O,O-diethyl N-(chlorothio)-n-propylphosphoramidothioate (prepared in Preparation I) is cooled in an ice-bath and 2.79 gm. (0.013 mole) of 4-(dimethylamino)-3,5-xylyl methylcarbamate dissolved in 20 ml dimethylformamide (with 2 ml triethylamine added) are mixed as a batch. This reaction mixture is stirred at 25° C. for four hours, and then diluted with hexane. The organic solution is washed with water, dried over anhydrous sodium sulfate, and the organic solvents are removed by evaporation under reduced pressure. The residue thus obtained is transferred to a column of "Florisil". The chromatogram is developed first with a solvent mixture consisting of 10 percent diethyl ether in petroleum ether, and finally with 30 percent diethyl ether in petroleum ether. After collecting the later eluate and removing the solvents by evaporation under reduced pressure, there is obtained the desired 4-(dimethylamino)-3,5-xylyl [[(diethoxyphosphinothioyl)-n-propylamino]thio]methylcarbamate as a yellow oil.

Workup

  1. additionare mixed as a batch
  2. washThe organic solution is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe organic solvents are removed by evaporation under reduced pressure
  5. customThe residue thus obtained
  6. customAfter collecting the later eluate
  7. customremoving the solvents
  8. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-bd38786dba574ae688e17087aaf30751
Source dataset
uspto-grants-1980_06
Patent number
US04208409

Reaction notes

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