Acetic Acid → 5-(2-Carboxy-alpha-methylbenzylidene)rhodanine

HRID 328986Notes

Reaction equation

HRID 328986 reaction equation
[C:1]([CH2:4][C:5]([C:7]1C=C[CH:10]=[CH:9][CH:8]=1)=O)(O)=O.[S:13]1[CH2:19][C:17](=[O:18])[NH:16][C:14]1=[S:15].[C:20]([OH:23])(=[O:22])[CH3:21].C([O-])(=O)C.[Na+]>O>[C:20]([C:21]1[CH:1]=[CH:4][CH:5]=[CH:7][C:8]=1[C:9](=[C:19]1[S:13][C:14](=[S:15])[NH:16][C:17]1=[O:18])[CH3:10])([OH:23])=[O:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 97045Benzoylacetic acidHCID 517045Sodium AcetateHCID 1201546Rhodanine

Product 1

HCID 737934855-(2-Carboxy-alpha-methylbenzylidene)rhodanine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a hot stirred solution of 2-carboxyacetophenone (1.91 g., 11.65 mM) and 1.57 g. (11.75 mM) of rhodanine in 8 ml. of acetic acid is added 3.12 g. (38.1 mM) of sodium acetate. The solution is refluxed for 3.5 hours, cooled, and poured into water, whereupon a gum forms. The gum crystallizes and is collected and recrystallized from methanol to give 5-(2-carboxy-α-methylbenzylidene) rhodanine as yellow-brown crystals, m.p. 193°-195°.

Workup

  1. temperatureThe solution is refluxed for 3.5 hours
  2. temperaturecooled
  3. customThe gum crystallizes
  4. customis collected
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-58087806d377466b9974f28fcd7f98da
Source dataset
uspto-grants-1977_04
Patent number
US04018891

Reaction notes

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