Potassium Hydroxide → HCID 15670615, compound

HRID 233775Notes

Reaction equation

HRID 233775 reaction equation
[OH-].[K+].C(OC([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([S:19][CH:20]1[S:24][C:23](=[O:25])[NH:22][C:21]1=[O:26])[CH:13]=[CH:12]2)=O)C>CO>[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([S:19][CH:20]1[S:24][C:23](=[O:25])[NH:22][C:21]1=[O:26])[CH:13]=[CH:12]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15670614HCID 15670614, compound

Product 1

HCID 15670615HCID 15670615, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (2.47 g, 44.0 mmol) was added to a suspension of 5-[(6-ethoxycarbonyloxy-2-naphthalenyl)thio]-2,4-thiazolidinedione (8.0 g, 22 mmol) in methanol (50 mL) at 25° C. After 30 minutes, the resulting solution was acidified to pH=1 with and then extracted with ethyl acetate (3×). The combined extracts were dried (magnesium sulfate) and concentrated to give 5-[(6-Hydroxyl-2-naphthalenyl)thio]-2,4-thiazolidinedione as a powder (6.4 g, 99% yield): mp 182°-183° C. (chloroform/ethyl acetate); 1H NMR (DMSO-d6, 400 MHz) δ6.07 (s, 1H CH). 7.1-8.0 (m, 6H, ArH). Analogue 35 was prepared similarly, with the use of 3 molar equivalents of potassium hydroxide.

Workup

  1. extractionthen extracted with ethyl acetate (3×)
  2. dry with materialThe combined extracts were dried (magnesium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3428b87be86f4ac7a4c0430d3a12f683
Source dataset
uspto-grants-1997_01
Patent number
US05594015

Reaction notes

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