Sodium Carbonate → 2-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acid

HRID 842004Notes

Reaction equation

HRID 842004 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:21]=[CH:20][C:12]([O:13][CH2:14][C:15]([O:17]CC)=[O:16])=[CH:11][CH:10]=2)[S:3]1.C([O-])([O-])=O.[Na+].[Na+]>CO.O>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:21]=[CH:20][C:12]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:11][CH:10]=2)[S:3]1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 10852377Ethyl 2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]acetate

Product 1

HCID 113234852-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acidYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirred solution of ethyl [4-[[2,4-dioxo-1,3-thiazolidine-5-yl]methyl]phenoxy]acetate (110 g, 0.36 mol) in methanol (0.65 L) was added as solution of Na2CO3 (200 g, 1.88 mol) in water (0.65 L) and stirred for 5 h at 25 to 30° C. After completion of the reaction, methanol was removed under reduced pressure; water was added to the residue and was acidified with hydrochlori acid. The precipitated white solid was filtered and dired to yield the title compound (80 g, 80%). mp: 181-183° C.

Workup

  1. customwas removed under reduced pressure
  2. additionwater was added to the residue
  3. filtrationThe precipitated white solid was filtered

Sources & evidence

ORD record
ord-289ea876952543fa9f673e42e29ff0ab
Source dataset
uspto-grants-2002_04
Patent number
US06372750B2

Reaction notes

Loading…