Beta-Alanine → HCID 19792088, compound

HRID 1885220Notes

Reaction equation

HRID 1885220 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[CH2:10][C:9]2([CH3:21])C=O)=[O:7])=[CH:4][CH:3]=1.[S:24]1[CH2:30][C:28](=[O:29])[N:27]([CH2:31][C:32]([OH:34])=[O:33])[C:25]1=[S:26].N[CH2:36]CC(O)=O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10](/[CH:36]=[C:30]3/[C:28](=[O:29])[N:27]([CH2:31][C:32]([OH:34])=[O:33])[C:25](=[S:26])[S:24]/3)=[C:9]2[CH3:21])=[O:7])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 797933-Thiazolidineacetic acid, 4-oxo-2-thioxo-HCID 86746103HCID 86746103, compound

Product 1

HCID 19792088HCID 19792088, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a room temperature solution of 1-(4-chlorobenzoyl)-5-methoxy-2 methylindole-carboxaldehyde (535 mg, 1.63 mmols) and rhodanine 3-acetic acid (345 mg, 1.80 mmols) in 15 mL of acetic acid is added β-alanine (142 mg, 1.59 mmols). The solution is heated at reflux for 1.5 hours, then allowed to cool to room temperature. Filtration, washing with acetic acid, then hexane, provides 458 mg (56%) of (Z)-5-[[1-(4 chlorobenzoyl)-5-methoxy-2-methyl-1H -indol-3-yl]methylene]-4-oxo-2-thioxo-3-thiazolidine acetic acid as a yellow solid. An analytical sample is obtained by two recrystallizations from acetonitrile: mp 204°-208° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 1.5 hours
  3. filtrationFiltration
  4. washwashing with acetic acid

Sources & evidence

ORD record
ord-9b74fc2742404d3e8c45543131be0642
Source dataset
uspto-grants-1992_09
Patent number
US05143927

Reaction notes

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