Sodium ethanethiolate → HCID 9966165, compound

HRID 722784Notes

Reaction equation

HRID 722784 reaction equation
C([S-])C.[Na+].[SH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([O-:22])=[O:21])[CH:15]=2)[C:9]=1[C:23]([O:25]C)=[O:24]>CN(C=O)C>[SH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([OH:22])=[O:21])[CH:15]=2)[C:9]=1[C:23]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 86587318HCID 86587318, compound

Product 1

HCID 9966165HCID 9966165, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
200 °C

Procedure

To a deoxygenated suspension of sodium ethanethiolate (0.135 g, 1.60 mmol) in DMF (0.5 mL) was added a solution of 3-(2-mercaptoethyl)-[1,1′-biphenyl]-2,3′-dicarboxylic acid, 2-methyl ester (0.10 g, 0.32 mmol) in DMF (0.5 mL). Argon was bubbled through the mixture for 10 min. The reaction was heated at 100° C. for 1 h and 200° C. for another hour. After the mixture cooled to rt, the reaction was quenched with 1 N HCl (20 mL) and was extracted with EtOAc (3×20 mL). The combined organic extracts were washed with water and brine, dried over MgSO4, filtered, and concentrated to afford 3-(2-mercaptoethyl)-[1,1′-biphenyl]-2,3′-dicarboxylic acid (0.055 g, 57%) as a white solid: 1H NMR (CDCl3) δ 1.51 (t, J=8.0 Hz, 1H), 2.87–2.93 (m, 2H), 3.12–3.08 (m, 2H), 7.37 (m, 2H), 7.57–7.47 (m, 2H), 7.70 (dm, J=7.9 Hz, 1H), 7.98 (dm, J=7.8 Hz, 1H), 8.30 (m, 1H); 13C NMR (CDCl3) δ 26.2, 38.8, 128.1, 129.3, 129.7, 129.8, 129.9 (2 C), 130.5, 133.3, 134.4, 137.7, 139.1, 141.2, 172.3, 176.9. Anal. Calcd for C16H14O4S: C, 63.56; H, 4.67; S, 10.61. Found: C, 63.65; H, 4.88; S, 10.33.

Workup

  1. customArgon was bubbled through the mixture for 10 min
  2. temperatureAfter the mixture cooled to rt
  3. customthe reaction was quenched with 1 N HCl (20 mL)
  4. extractionwas extracted with EtOAc (3×20 mL)
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5488f2d8bd33445292befa1afee51bd4
Source dataset
uspto-grants-2006_11
Patent number
US07138543B2

Reaction notes

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