Sodium Acetate → 5-[(3,4-Diethoxyphenyl)methyl]-2-imino-1,3-thiazolidin-4-one

HRID 354686Notes

Reaction equation

HRID 354686 reaction equation
Cl[CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[C:11]([O:18][CH2:19][CH3:20])[CH:10]=1)[C:3](OCC)=[O:4].[NH2:21][C:22]([NH2:24])=[S:23].C([O-])(=O)C.[Na+]>COCCO>[CH2:19]([O:18][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[O:15][CH2:16][CH3:17])[CH2:8][CH:2]1[S:23][C:22](=[NH:21])[NH:24][C:3]1=[O:4])[CH3:20]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 13103729Ethyl 2-chloro-3-(3,4-diethoxyphenyl)propionate

Product 1

HCID 1403385215-[(3,4-Diethoxyphenyl)methyl]-2-imino-1,3-thiazolidin-4-oneYield 65.5%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
110 °C

Procedure

In 120 ml of ethylene glycol monomethyl ether is dissolved 11.7 g of ethyl 2-chloro-3-(3,4-diethoxyphenyl)propionate, followed by addition of 4.4 g of thiourea and 3.8 g of sodium acetate. The mixture is stirred at 110° C. for 15 hours. The solvent is distilled off under reduced pressure, water is added to the residue and extraction is carried out with ethyl acetate. The extract is washed with water, dried (over MgSO4) and distilled to remove the ethyl acetate. The above procedure provides 7.5 g (65.2%) of 5-(3,4-diethoxybenzyl)-2-iminothiazolidin-4-one as crystals melting at 171°-172° C.

Workup

  1. distillationThe solvent is distilled off under reduced pressure, water
  2. additionis added to the residue and extraction
  3. washThe extract is washed with water
  4. dry with materialdried (over MgSO4)
  5. distillationdistilled
  6. customto remove the ethyl acetate

Sources & evidence

ORD record
ord-d1d8f70134a4463488559c621bd5eb55
Source dataset
uspto-grants-1983_03
Patent number
US04376777

Reaction notes

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