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

HRID 977197

Reaction equation

HRID 977197 reaction equation
[S:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[S:3].[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>C(O)(=O)C>[OH:8][C:9]1[CH:10]=[C:11]([CH:12]=[C:7]2[S:1][C:2](=[S:3])[NH:4][C:5]2=[O:6])[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[C:16]=1[OH:17]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 1201546RhodanineHCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde

Product 1

HCID 538621515-[(3,4-Dihydroxy-5-nitrophenyl)methylidene]-2-thioxothiazolidin-4-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution containing 2.1 g (0.0157 mol) of rhodanine, 2.76 g (0.0151 mol) of 3,4-dihydroxy-5-nitrobenzaldehyde and 0.15 ml of piperidine in 10 ml of acetic acid was heated for 7-8 h at 100° C. After cooling the crystals were filtered and washed with 2-propanol. Yield 4.0 g (89%), mp >350° C. (decomp.).

Workup

  1. temperatureAfter cooling the crystals
  2. filtrationwere filtered
  3. washwashed with 2-propanol

Sources & evidence

ORD record
ord-66addbede7dd4f95a1f4c797e968fe42
Source dataset
uspto-grants-1997_03
Patent number
US05614541

Linked notes

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