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

HRID 1607054Notes

Reaction equation

HRID 1607054 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 3N HCl (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 3N HCl (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-8a97d486ba6f4c5c89c22ebfaecf51e2
Source dataset
uspto-grants-1989_09
Patent number
US04863922

Reaction notes

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