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

HRID 2078470Notes

Reaction equation

HRID 2078470 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-758362162e794260927e2f6871304bef
Source dataset
uspto-grants-2011_04
Patent number
US07928246B2

Reaction notes

Loading…