Hydrochloric Acid → HCID 131719366, compound

HRID 1720189Notes

Reaction equation

HRID 1720189 reaction equation
[O:1]1[CH:6]([C:7]([OH:9])=[O:8])[CH:2]1[C:3]([OH:5])=[O:4].[Na][Na].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.[OH-].[Na+].Cl>O>[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]/[C:6](=[C:2](\[OH:1])/[C:3]([OH:5])=[O:4])/[C:7]([OH:9])=[O:8])=[CH:15][CH:14]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 145104-AminothiophenolHCID 14798Sodium HydroxideHCID 86022Epoxysuccinic acidHCID 141233DisodiumHCID 178435160HCID 178435160, compound

Product 1

HCID 131719366HCID 131719366, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 70 percent epoxysuccinic acid, disodium salt (6.573 g, 26 14 mmol) in 25 mL water was added a filtered solution of 4-aminothiophenol (3.251 g, 25.97 mmol) in aq NaOH (28 mmol in 20 mL of water) via polyethylene cannula under nitrogen with stirring. After 22 hours, the cloudy reaction mixture was washed with 30 mL of ether and then acidified to pH 3 with 6M HCl, (13.3 mL, 79.8 mmol) producing a white solid precipitate. The solid was washed with 20 mL of water and dried (70° C., 0.05 mm Hg vacuum) to afford 3.364 g, (50 percent of theoretical) of 2-[4'-(amino)thiophenoxy]-3-hydroxymaleic acid; 1H NMR (DMSO-d6, d) 8.1 (2H, br), 7.13 (2H, d, J=8.3 Hz), 6.48 (2H, d, J=8.3 Hz), 4.05 (2H, d, J=7.6 Hz), 3.47 (2H, d, J=7.6 Hz); 13C NMR (DMSO-d6, d) 173.1, 171.3, 149.4, 136.0, 116.2, 114.1, 70.4, 56.0; IR (Nujol mull, cm-1) 3410 (br, m), 1710 (br, m).

Workup

  1. customthe cloudy reaction mixture
  2. washwas washed with 30 mL of ether
  3. customproducing a white solid precipitate
  4. washThe solid was washed with 20 mL of water
  5. customdried (70° C., 0.05 mm Hg vacuum)

Sources & evidence

ORD record
ord-51580036d2ec4693b91e57c2b6f4b8f8
Source dataset
uspto-grants-1996_04
Patent number
US05505931

Reaction notes

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