Thioglycolic Acid → 2-[[3-oxo-2-(thiophen-2-ylmethyl)-1H-isoindol-1-yl]sulfanyl]acetic Acid

HRID 492229Notes

Reaction equation

HRID 492229 reaction equation
O[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1.[C:18]([OH:22])(=[O:21])[CH2:19][SH:20]>C(O)(=O)C>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:2]([S:20][CH2:19][C:18]([OH:22])=[O:21])[N:3]1[CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 1133Thioglycolic AcidHCID 4616003HCID 4616003, compound

Product 1

HCID 36971622-[[3-oxo-2-(thiophen-2-ylmethyl)-1H-isoindol-1-yl]sulfanyl]acetic AcidYield 83.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of compound 12 (5.45 gm, 22.2 mmol) in acetic acid (50 mL) at room temperature was added thioglycolic acid (1.85 mL, 26.7 mmol) and the resulting reaction mixture was allowed to stir at reflux for 18 hours. The reaction mixture was concentrated in vacuo and triturated with ethyl ether to provide 5.9 gm of 15 as a white solid (7.08 gm theoretical, 83% yield).

Workup

  1. customthe resulting reaction mixture
  2. temperatureat reflux for 18 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customtriturated with ethyl ether

Sources & evidence

ORD record
ord-86218ce5d11b495d82cf4d8662aa38f2
Source dataset
uspto-grants-2009_05
Patent number
US07531671B2

Reaction notes

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