Acetic Anhydride → HCID 54431541, compound

HRID 364864Notes

Reaction equation

HRID 364864 reaction equation
[C:1]([CH2:4][N:5]1[C:9](=[O:10])[CH2:8][S:7][C:6]1=[S:11])([OH:3])=[O:2].[CH:12]([O-])([O-])[O:13][CH2:14][CH3:15].C(OC(=O)C)(=O)C>>[C:1]([CH2:4][N:5]1[C:9](=[O:10])[C:8](=[CH:12][O:13][CH2:14][CH3:15])[S:7][C:6]1=[S:11])([OH:3])=[O:2]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 797933-Thiazolidineacetic acid, 4-oxo-2-thioxo-HCID 53630039Ethylorthoformate

Product 1

HCID 54431541HCID 54431541, compoundYield 62.5%

Procedure

A mixture of 36 g (0.189 mole) of 3-carboxymethylrhodanine, 33.6 g (0.225 mole) of ethyl orthoformate and 225 ml of acetic anhydride was subjected to reactiqn under reflux for about 1 to 2 hours and then the reaction mixture was concentrated. A precipitate was formed by the addition of a small amount of chloroform to the residue. The precipitate was separated and recrystallized from ethyl acetate to give 29.2 g of 3-carboxymethyl-5-ethoxymethylidenerhodanine in the form of brownish white crystal (yield: 62.5 %).

Workup

  1. temperatureunder reflux for about 1 to 2 hours
  2. concentrationthe reaction mixture was concentrated
  3. customA precipitate was formed by the addition of a small amount of chloroform to the residue
  4. customThe precipitate was separated
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-bef4ef66317f45f3a3105bcc68665c5f
Source dataset
uspto-grants-1986_08
Patent number
US04606860

Reaction notes

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