Acetic Acid → 5-(2-Phenylpyrazolo[1,5-a]pyridine-3-yl)methylenerhodanine

HRID 466005Notes

Reaction equation

HRID 466005 reaction equation
[C:1]1([C:7]2[C:15]([CH:16]=O)=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:18]1[CH2:24][C:22](=[O:23])[NH:21][C:19]1=[S:20].C([O-])(=O)C.[Na+].C(O)(=O)C>C(OCC)(=O)C.O>[C:1]1([C:7]2[C:15]([CH:16]=[C:24]3[S:18][C:19](=[S:20])[NH:21][C:22]3=[O:23])=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 1201546RhodanineHCID 151581792-Phenylpyrazolo[1,5-a]pyridine-3-carbaldehyde

Product 1

HCID 544516175-(2-Phenylpyrazolo[1,5-a]pyridine-3-yl)methylenerhodanineYield 86.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-phenylpyrazolo[1,5-a]pyridine-3-carbaldehyde (15.0 g), rhodanine (9.44 g), sodium acetate (16.6 g) and glacial acetic acid (90 ml) was refluxed for 10 hours. Water (200 ml) and ethyl acetate (90 ml) were added to the reaction mixture and the resulting precipitates were collected by filtration to give 5-(2-phenylpyrazolo[1,5-a]pyridine-3-yl)methylenerhodanine (cis and trans mixture) (19.8 g).

Workup

  1. temperaturewas refluxed for 10 hours
  2. customthe resulting precipitates
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-147b809a9c654ab7b189480179e3c057
Source dataset
uspto-grants-1992_10
Patent number
US05155114

Reaction notes

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