Triethylamine → HCID 20137392, compound

HRID 1981858Notes

Reaction equation

HRID 1981858 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](O)=O.C([S:17](=S)OCC)C.C(N([CH2:27][CH3:28])CC)C>C(Cl)(Cl)Cl>[CH2:27]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([SH:17])=[S:1])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 54350211-Mercaptoundecanoic AcidHCID 53842069HCID 53842069, compound

Product 1

HCID 20137392HCID 20137392, compoundYield 111.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 11-mercaptoundecanoic acid (1.40 g, 6.42 mmol), ethyl ethanethiosulfinate (1.18 g, 8.55 mmol) and triethylamine (0.72 mL, 5.2 mmol) in 16 mL of chloroform was stirred at room temperature for 24 hours. Evaporation of solvent under reduced pressure followed by chromatographic purification of the residue on a silica gel column (2.5×40 cm), eluting first with CHCl3 and then solvent A, furnished 1.43 g (80%) of 11-ethyldithioundecanoic acid; Rf =0.52 (5% CH3OH in CHCl3); IR(nujol) νC=O 1700 cm-1 ; 1H NMR(CDCl3) 1.3 (br s and t, 19H, CH2 and CH3CH2S), 2.33 (t, 2H, CH2CO), 2.45-2.9 (m, 4H, CH2S), 11.7 (s, 1H, CO2H).

Workup

  1. customEvaporation of solvent under reduced pressure
  2. customfollowed by chromatographic purification of the residue on a silica gel column (2.5×40 cm)
  3. washeluting first with CHCl3

Sources & evidence

ORD record
ord-0cbba304d34d45f7be9accdd570d29a4
Source dataset
uspto-grants-1986_06
Patent number
US04594193

Reaction notes

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