HCID 13713937, compound → HCID 86741993, compound

HRID 4407Notes

Reaction equation

HRID 4407 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:29]=[CH:28][C:19](/[CH:20]=[C:21]2/[C:22](=[O:27])[NH:23][C:24](=[O:26])[S:25]/2)=[CH:18][CH:17]=1>C(#N)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:29]=[CH:28][C:19](/[CH:20]=[C:21]2\[C:22](=[O:27])[NH:23][C:24](=[O:26])[S:25]\2)=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 13713937HCID 13713937, compound

Product 1

HCID 86741993HCID 86741993, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (Z)-5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione (200 mg) in acetonitrile (750 ml), in a quartz tube under a stream of nitrogen, was irradiated by a 300 W high-pressure mercury lamp for 3 hours. The solvent was distilled off, and the resulting crystals were chromatographed on a column of silica gel (200 g). Elution with hexane-ethyl acetate (1:1, V/V) gave (E)-5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione (40 mg, 20.0%). Recrystallization from dichloromethaneethanol yielded colorless needles, m.p. 216°-217° C. Elemental analysis for C22H18N2O4S; Calcd.: C, 65.01; H, 4.46; N, 6.89. Found: C, 64.69; H, 4.26; N, 7.11. The subsequent elution with hexane-ethyl acetate (1:1, V/v) allowed the recovery of (Z)-5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione (138 mg, 69.0%).

Workup

  1. distillationThe solvent was distilled off
  2. customthe resulting crystals were chromatographed on a column of silica gel (200 g)
  3. washElution with hexane-ethyl acetate (1:1, V/V)

Sources & evidence

ORD record
ord-760057bc35304f8ba2f1de1ab245109e
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Reaction notes

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