Methane → 2-(Pyridin-4-yl)-1,3-thiazolidine-4-carboxylic acid

HRID 704368Notes

Reaction equation

HRID 704368 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[NH2:9][C@H:10]([C:13]([OH:15])=[O:14])[CH2:11][SH:12].C>C(O)C>[N:1]1[CH:2]=[CH:3][C:4]([CH:7]2[NH:9][CH:10]([C:13]([OH:15])=[O:14])[CH2:11][S:12]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 5862L-(+)-CysteineHCID 133894-Pyridinecarboxaldehyde

Product 1

HCID 999852-(Pyridin-4-yl)-1,3-thiazolidine-4-carboxylic acidYield 57.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pyridine-4-carbaldehyde (1.07 g) and 1.21 g of L-cysteine were heated in 60% ethanol at a refluxing temperature for 4 hours. Activated charcoal (100 mg) was added to the reaction mixture while it was warm. The mixture was filtered. After cooling, the resultant crystalline precipitate was collected by filtration and washed with ethanol to give 1.2 g of 2-(4-pyridyl)thiazolidine-4-carboxylic acid. Melting point 171°-173° C.

Workup

  1. temperaturewas warm
  2. filtrationThe mixture was filtered
  3. temperatureAfter cooling
  4. filtrationthe resultant crystalline precipitate was collected by filtration
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-ccfb367f4fd843feb2efafa3ec8a9a12
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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