Beta-Alanine → HCID 19792088, compound

HRID 1655398Notes

Reaction equation

HRID 1655398 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-methylindolecarboxaldehyde (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-866eccc7cd24448da7b748b92eb60294
Source dataset
uspto-grants-1993_10
Patent number
US05250552

Reaction notes

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