Phosphorodithioate → Methyl 3-thiocarbamoylmethoxybenzoate

HRID 1602496Notes

Reaction equation

HRID 1602496 reaction equation
P([O-])([O-])([S-])=[S:2].[C:6]([CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])#[N:7]>C(OCC)(=O)C.Cl>[C:6]([CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])(=[S:2])[NH2:7]

Participants

4

Reactant 2

HCID 177047PhosphorodithioateHCID 14917017Methyl 3-(cyanomethoxy)benzoate

Product 1

HCID 19611422Methyl 3-thiocarbamoylmethoxybenzoateYield 78%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

4 N Hydrogen chloride-ethyl acetate solution (50 ml) and dithiophosphate=O,O-diethyl (4.47 ml, 26.67 mmol) were added in that order to methyl 3-cyanomethoxybenzoate (5.00 g, 26.15 mmol), and the resulting solution was stirred at room temperature for 12 hours. Crystals precipitated in the reaction solution were collected by filtration and washed with diethyl ether to give methyl 3-thiocarbamoylmethoxybenzoate (4.60 g, 78%).

Workup

  1. customCrystals precipitated in the reaction solution
  2. filtrationwere collected by filtration
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-443c714b642b44efbe4a71e33896aeaa
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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