Triethylamine → S-sec-butyl ethylphosphonotrithioic acid

HRID 2118481Notes

Reaction equation

HRID 2118481 reaction equation
C(N(CC)CC)C.[CH2:8]([P:10](=[S:12])=[S:11])[CH3:9].[CH:13]([SH:17])([CH2:15][CH3:16])[CH3:14]>O1CCCC1>[CH:13]([S:17][P:10]([CH2:8][CH3:9])([SH:12])=[S:11])([CH2:15][CH3:16])[CH3:14]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 105602-ButanethiolHCID 16131073Phosphenodithioic ethane

Product 1

HCID 13564051S-sec-butyl ethylphosphonotrithioic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The triethylamine salt of S-(sec-butyl)ethylphosphonotrithioic acid was prepared as follows: 14.0 g (0.056 mole) of ethyl thionophosphine sulfide was dissolved in tetrahydrofuran; then 11.2 g (0.124 mole) of sec-butyl mercaptan was added, all at once. Then, 11.3 g (0.112 mole) triethylamine was added dropwise. The mixture was stirred at room temperature, then refluxed for 15 minutes. The solvent was removed in vacuo, leaving the acid salt (24.1 g, 68% of theoretical yield) as a semi-solid.

Workup

  1. temperaturerefluxed for 15 minutes
  2. customThe solvent was removed in vacuo
  3. customleaving
  4. customthe acid salt (24.1 g, 68% of theoretical yield) as a semi-solid

Sources & evidence

ORD record
ord-1ec2a2b5ba834f4e859123c20538a968
Source dataset
uspto-grants-1987_07
Patent number
US04678778

Reaction notes

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