Triethylamine → 2-[(Thiophen-2-yl)sulfanyl]butanedioic acid

HRID 620518Notes

Reaction equation

HRID 620518 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[SH:14].C(N(CC)CC)C>O1CCCC1>[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[S:14][CH:3]([CH2:2][C:1]([OH:8])=[O:7])[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 444266Maleic AcidHCID 5226742-Thiophenethiol

Product 1

HCID 43659042-[(Thiophen-2-yl)sulfanyl]butanedioic acidYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of maleic acid (6.38 g, 0.055 mol) in tetrahydrofuran (50 ml) under nitrogen atmosphere was added 2-thiophenethiol (5.0 ml, 0.055 mol) and triethylamine (14.2 g, 0.14 mol). The mixture was stirred at gentle reflux for 16 hours overnight. The solvent was removed in vacuo and the residual oil was poured into 3NHCl (200 ml). The product was extracted into ethyl acetate (125 ml) in three portions, washed with saturated NaCl solution and dried over Na2SO4. The solution was filtered and concentrated in vacuo. This procedure gave the product as a light beige solid, 11.9 g, m.p. 136°-138.5° C. of 95% purity by HPLC. Yield was 93%.

Workup

  1. temperatureat gentle reflux for 16 hours overnight
  2. customThe solvent was removed in vacuo
  3. additionthe residual oil was poured into 3NHCl (200 ml)
  4. extractionThe product was extracted into ethyl acetate (125 ml) in three portions
  5. washwashed with saturated NaCl solution
  6. dry with materialdried over Na2SO4
  7. filtrationThe solution was filtered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0a67d86f908483790fc533713eeb0a4
Source dataset
uspto-grants-1989_04
Patent number
US04820848

Reaction notes

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