Water → HCID 13648316, compound

HRID 1982348Notes

Reaction equation

HRID 1982348 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:29]=[CH:28][C:11]2[N:12]=[C:13]([O:15][C:16]3[CH:27]=[CH:26][C:19]([O:20][CH:21]([CH3:25])[C:22]([OH:24])=[O:23])=[CH:18][CH:17]=3)[S:14][C:10]=2[CH:9]=1.Cl[CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33].O>CN(C)C=O>[Cl:7][C:8]1[CH:29]=[CH:28][C:11]2[N:12]=[C:13]([O:15][C:16]3[CH:27]=[CH:26][C:19]([O:20][CH:21]([CH3:25])[C:22]([O:24][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])=[O:23])=[CH:18][CH:17]=3)[S:14][C:10]=2[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 75361Silane, (chloromethyl)trimethyl-HCID 156003Fenthiaprop

Product 1

HCID 13648316HCID 13648316, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2.9 g of potassium carbonate are added to a solution of 6.2 g (0.179 mole) of the R-enantiomer of 2-{4-[(6-chloro-2-benzothiazolyl)-oxy]-phenoxy}-propionic acid in 20 ml of dimethylformamide. After the mixture has been stirred at 50° C. for 15 minutes, 2.7 g (0.021 mole) of chloromethyltrimethylsilane are added dropwise at this temperature. The mixture is then subsequently stirred at 80° C. for 2 hours. It is then worked up by stripping off the solvent under reduced pressure, adding water to the residue and extracting the resulting oily product with 100 ml of toluene. The organic phase is washed successively with aqueous sodium carbonate solution and with water, dried and concentrated under reduced pressure. 7 g (89% of theory) of the R-enantiomer of trimethylsilyl-methyl 2-{4-[(6-chloro-2-benzothiazolyl)-oxy]-phenoxy}-propionate are obtained in this manner in the form of a viscous oil.

Workup

  1. stirringThe mixture is then subsequently stirred at 80° C. for 2 hours
  2. extractionextracting the resulting oily product with 100 ml of toluene
  3. washThe organic phase is washed successively with aqueous sodium carbonate solution and with water
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-844ac2e852584342a88e9209b38018ee
Source dataset
uspto-grants-1986_06
Patent number
US04596594

Reaction notes

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