Dibromomethane → 1-[Ethoxy(isothiocyanato)phosphoryl]oxyethane

HRID 1833903Notes

Reaction equation

HRID 1833903 reaction equation
[Na].[K].[S-:3][C:4]#[N:5].[NH4+].C(Br)Br.[CH2:10]([O:12][P:13](Cl)([O:15][CH2:16][CH3:17])=[O:14])[CH3:11]>C(Cl)Cl.C(Cl)(Cl)Cl.C(Cl)CCl.C1(C)C(C)=CC=CC=1.C1(C)C=CC=CC=1.C1C=CC=CC=1>[CH2:10]([O:12][P:13]([N:5]=[C:4]=[S:3])([O:15][CH2:16][CH3:17])=[O:14])[CH3:11]

Participants

12

Reactant 5

HCID 3024DibromomethaneHCID 13139Diethyl chlorophosphateHCID 15666Ammonium thiocyanateHCID 5360545SodiumHCID 5462222Potassium

Product 1

HCID 5568321-[Ethoxy(isothiocyanato)phosphoryl]oxyethane

Reagents, catalysts & solvents 6

HCID 111,2-DichloroethaneSolventHCID 241BenzeneSolventHCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 7237O-XyleneSolvent

Procedure

To a stirred slurry of 1.0 to 1.2 molar equivalent of anhydrous sodium-, potassium- or ammonium thiocyanate in about 50 ml to 100 ml of a solvent, such as benzene, toluene, xylene, ethylene dichloride, chloroform, methylene chloride and methylene bromide, one molar equivalent of diethoxyphosphoryl chloride of formula (II) is added at a temperature range of 5° to 30° C and, preferably, from 15° to 25° C, while stirring for a period of time from 2 to 4 hours to yield diethoxyphosphinyl isothiocyanate of formula (III). The reaction is slightly exothermic, and controlled by either adjusting the rate of addition of said phosphoryl chloride or employing a cooling bath or even using both.

Sources & evidence

ORD record
ord-194dbc34027e4946a03b8e1fdda278a1
Source dataset
uspto-grants-1978_01
Patent number
US04067882

Reaction notes

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