Piperidine → 5-[(3,4-Dihydroxy-5-nitrophenyl)methylidene]-4-thioxothiazolidin-2-one

HRID 977200Notes

Reaction equation

HRID 977200 reaction equation
[S:1]=[C:2]1[CH2:6][S:5][C:4](=[O:7])[NH:3]1.[OH:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[C:16]=1[OH:17])[CH:12]=O.N1CCCCC1>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[OH:8][C:9]1[CH:10]=[C:11]([CH:12]=[C:6]2[S:5][C:4](=[O:7])[NH:3][C:2]2=[S:1])[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[C:16]=1[OH:17]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde

Product 1

HCID 1360589475-[(3,4-Dihydroxy-5-nitrophenyl)methylidene]-4-thioxothiazolidin-2-one

Reagents, catalysts & solvents 1

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Conditions

Temperature
100 °C

Procedure

A solution containing 0.67 g (0.005 mol) of 4-thioxothiazolidin-2-one, 0.92 g (0.005 mol) of 3,4-dihydroxy-5-nitrobenzaldehyde and 0.05 ml of piperidine in 10 ml of acetic was heated for 8 h at 100° C. The product was filtered and washed with 2-propanol. Yield 1.14 g (76.5%), mp >350° C. (decomp.).

Workup

  1. filtrationThe product was filtered
  2. washwashed with 2-propanol

Sources & evidence

ORD record
ord-bc7f4ba644324b02b4544684d4187c82
Source dataset
uspto-grants-1997_03
Patent number
US05614541

Reaction notes

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