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

HRID 129724Notes

Reaction equation

HRID 129724 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-09efa1ff6f7d48a08bf9697de6c52e06
Source dataset
uspto-grants-1995_11
Patent number
US05470851

Reaction notes

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