Sodium Acetate → 5-(2-Carboxy-3-methoxybenzylidene)rhodanine

HRID 328983Notes

Reaction equation

HRID 328983 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH:12]=O)[C:8]=1[C:9]([OH:11])=[O:10].[S:14]1[CH2:20][C:18](=[O:19])[NH:17][C:15]1=[S:16].C([O-])(=O)C.[Na+]>C(O)(=O)C>[C:9]([C:8]1[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=1[CH:12]=[C:20]1[S:14][C:15](=[S:16])[NH:17][C:18]1=[O:19])([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 1201546RhodanineHCID 40975672-Formyl-6-methoxybenzoic acid

Product 1

HCID 543067415-(2-Carboxy-3-methoxybenzylidene)rhodanine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred hot solution of 2.10 g. (11.65 mM) of 6-methoxyphthalaldehydic acid 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 resulting solution is refluxed 0.5 hour and then poured into ice water to give a tan precipitate. The solid is collected and partially air-dried to give 5-(2-carboxy-3-methoxybenzylidene)rhodanine as a tan solid.

Workup

  1. temperatureThe resulting solution is refluxed 0.5 hour
  2. customto give a tan precipitate
  3. customThe solid is collected
  4. custompartially air-dried

Sources & evidence

ORD record
ord-8377a3225c814ae68d85ac165e05c747
Source dataset
uspto-grants-1977_04
Patent number
US04018891

Reaction notes

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