Ethanethiol → 2-chloroethanethiophosphonic acid S-ethyl ester N-monoisopropylamide

HRID 462011Notes

Reaction equation

HRID 462011 reaction equation
[CH2:1]([SH:3])[CH3:2].C(N(CC)CC)C.[Cl-].[CH:12]([NH:15][P:16]([CH2:19][CH2:20][Cl:21])(=[O:18])[OH:17])([CH3:14])[CH3:13]>C1C=CC=CC=1>[CH:12]([NH-:15])([CH3:14])[CH3:13].[CH2:1]([S:3][P:16]([CH2:19][CH2:20][Cl:21])(=[O:17])[OH:18])[CH3:2]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 8471TriethylamineHCID 867353082-chloroethanephosphonic acid N-monoisopropylamide chloride

Product 1

HCID 867353102-chloroethanethiophosphonic acid S-ethyl ester N-monoisopropylamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

13 g (0.2 mole) ethylmercaptan and 20 g (0.2 mole) triethylamine are added to 41 g (0.2 mole) 2-chloroethanephosphonic acid N-monoisopropylamide chloride in 100 ml benzene. Stirring was afterwards effected for 2 hours at 40° C; the salts were then filtered off with suction, the reaction solution was washed with water, and drying with sodium sulfate was carried out. After the solvent had been drawn off, there remained behind a crystalline residue, m.p. 51° C, yield: 15 g (33%) 2-chloroethanethiophosphonic acid S-ethyl ester N-monoisopropylamide.

Workup

  1. filtrationthe salts were then filtered off with suction
  2. washthe reaction solution was washed with water
  3. dry with materialdrying with sodium sulfate

Sources & evidence

ORD record
ord-f7e0b7a378554beaa6617603c1906cbe
Source dataset
uspto-grants-1977_12
Patent number
US04065288

Reaction notes

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