Water → HCID 178518565, compound

HRID 1296802Notes

Reaction equation

HRID 1296802 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=O)=[CH:2]1.[S:12]1[CH2:18][C:16](=[O:17])[NH:15][C:13]1=[S:14].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:18]2[S:12][C:13](=[S:14])[NH:15][C:16]2=[O:17])=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 1201546RhodanineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

Product 1

HCID 178518565HCID 178518565, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The suspension of 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (example 1b, 1.2 g, 8.22 mmol), rhodanine (1.09 g, 8.22 mmol) and sodium acetate (2.69 g, 32.8 mmol) in acetic acid (12 mL) was stirred under reflux for 12 h. After cooling to room temperature, water (150 mL) was added. The solid was collected by filtration, washed with water and dried to obtain 5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-2-thioxo-thiazolidin-4-one (2.2 g, 100%) as a brawn solid. LC-MS m/e 262 (MH+).

Workup

  1. temperatureunder reflux for 12 h
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-3658cd7b52084b299d58b0840e708010
Source dataset
uspto-grants-2007_07
Patent number
US07247727B2

Reaction notes

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