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

HRID 703964Notes

Reaction equation

HRID 703964 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 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]pyridin-3-yl)methylenerhodanine (cis and trans mixture) (19.8 g).

Workup

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

Sources & evidence

ORD record
ord-93c75b3ca8d1406f8c3cd9eb6f37d826
Source dataset
uspto-grants-1991_01
Patent number
US04985444

Reaction notes

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