Triethylamine hydrochloride → O,O-diethyl N-(chlorothio)-n-propylphosphoramidothioate

HRID 1706706Notes

Reaction equation

HRID 1706706 reaction equation
[CH2:1]([NH:4][P:5](=[S:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8])[CH2:2][CH3:3].[S:13](Cl)[Cl:14].Cl.C(N(CC)CC)C>CCCCCC.C(N(CC)CC)C>[Cl:14][S:13][N:4]([CH2:1][CH2:2][CH3:3])[P:5](=[S:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 25353Sulfur dichlorideHCID 2172696O,O-diethyl propylphosphoramidothioate

Product 1

HCID 20333951O,O-diethyl N-(chlorothio)-n-propylphosphoramidothioate

Reagents, catalysts & solvents 2

HCID 8058HexaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

A solution of 2.98 gm. (0.014 mole) O,O-diethyl n-propylphosphoramidothioate in 10 ml. hexane and 2 ml. triethylamine is added to a cold (0° C.) solution of 1.0 ml. (0.016 mole) sulfur dichloride in 10 ml. hexane slowly and with stirring. There is vigorous reaction and heavy precipitation of triethylamine hydrochloride. An additional 20 ml. hexane is added. The reaction mixture is kept at 0° to 5° C. and stirred for 30 minutes, then it is filtered. The filtrate is concentrated to a pale yellow oil by evaporating the hexane under reduced pressure. The oil comprises the desired O,O-diethyl N-(chlorothio)-n-propylphosphoramidothioate which can be used for further reactions with N-methylcarbamates.

Workup

  1. customis kept at 0° to 5° C.
  2. filtrationit is filtered
  3. concentrationThe filtrate is concentrated to a pale yellow oil
  4. customby evaporating the hexane under reduced pressure

Sources & evidence

ORD record
ord-eb62bfc35fec4a00bf1f1371c41c0480
Source dataset
uspto-grants-1980_06
Patent number
US04208409

Reaction notes

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