2-Naphthol → 5-(2-Naphthalenyloxy)-2,4-thiazolidinedione

HRID 399770Notes

Reaction equation

HRID 399770 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].Br[CH:13]1[S:17][C:16](=[O:18])[NH:15][C:14]1=[O:19].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C(Cl)(Cl)Cl.C(#N)C>C1COCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH:13]1[S:17][C:16](=[O:18])[NH:15][C:14]1=[O:19]

Participants

6

Reactant 4

HCID 86632-NaphtholHCID 2733832Lithium HexamethyldisilazideHCID 34937495-Bromothiazolidine-2,4-dioneHCID 22555007Acetonitrile chloroform

Product 1

HCID 442803915-(2-Naphthalenyloxy)-2,4-thiazolidinedioneYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By a procedure similar to that of method B, a solution of 2-naphthol (5.0 g, 35 mmol) and 5-bromo-2,4-thiazolidinedione (6.8 g, 35 mmol) in THF (200 mL) was treated with lithium bis(tri-methylsilyl)amide (76 mL, 76 mmol, 1.0M in THF) to give, after chromatography (acid-washed silica gel, chloroform/acetonitrile), 5-(2-Naphthalenyloxy)-2,4-thiazolidinedione (2.8 g, 31% yield): mp 221°-222° C. (acetone/ethyl acetate); 1H NMR (DMSO-d6, 400 MHz) δ 6.52 (s, 1 H, OCH), 7.1-8.0 (m, 6 H, ArH), 10.57 (s, 1 H, ArH).

Workup

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Sources & evidence

ORD record
ord-8e204a73e54e49e588521b93e5541bcd
Source dataset
uspto-grants-1998_10
Patent number
US05824694

Reaction notes

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