Water → HCID 22416575, compound

HRID 1721221Notes

Reaction equation

HRID 1721221 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[S:3]1.[H-].[Na+].[C:18]1([CH2:26]Br)[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][CH:19]=1.[OH2:28]>CN(C)C=O.C(OCC)(=O)C>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:26][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][O:28][C:12]4[CH:11]=[CH:10][C:9]([CH2:8][CH:4]5[S:3][C:2](=[O:1])[NH:6][C:5]5=[O:7])=[CH:14][CH:13]=4)=[CH:20][CH:19]=3)=[CH:11][CH:10]=2)[S:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 693351,4-Bis(bromomethyl)benzeneHCID 101983975-(4-Hydroxybenzyl)thiazolidine-2,4-dione

Product 1

HCID 22416575HCID 22416575, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A 2.23 g portion of 2,4-dioxo-5-[(p-hydroxyphenyl)-methyl]thiazolidine was dissolved in 25 ml of dimethylformamide, and the solution was mixed with 0.8 g of sodium hydride and maintained at 60° C. for 3 hours. Under cooling with ice water, 1.32 g of p-xylylene dibromide was added to the solution, and the mixture was incubated at room temperature for 3 hours and then at 80° C. for 3 hours. A 100 ml portion of water and 100 ml of ethyl acetate were added to the reaction mixture to dissolve insoluble contents, and the resulting organic layer was collected and washed with water, followed by distillation to remove ethyl acetate. Thereafter, the resulting residue was subjected to silica gel column chromatography (eluent: chloroform) to obtain 1,4-bis[[4-[(2,4-dioxo-5-thiazolidinyl)methyl]phenoxy]methyl]benzene.

Workup

  1. additionwas added to the solution
  2. waitat 80° C. for 3 hours
  3. dissolutionto dissolve insoluble contents
  4. customthe resulting organic layer was collected
  5. washwashed with water
  6. distillationfollowed by distillation
  7. customto remove ethyl acetate

Sources & evidence

ORD record
ord-79cf0a9a4c2546c1baa926b161924e3a
Source dataset
uspto-grants-1996_04
Patent number
US05508296

Reaction notes

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