Sulfolane → HCID 13488878, compound

HRID 1589685Notes

Reaction equation

HRID 1589685 reaction equation
Cl[CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2([CH3:32])[CH2:27][CH2:26][C:25]3[C:20](=[C:21]([CH3:31])[C:22]([CH3:30])=[C:23]([OH:29])[C:24]=3[CH3:28])[O:19]2)=[CH:11][CH:10]=1)[C:3](OCC)=[O:4].[NH2:33][C:34](N)=[S:35].S1(CCCC1)(=O)=[O:38]>C(OCC)(=O)C>[OH:29][C:23]1[C:24]([CH3:28])=[C:25]2[C:20](=[C:21]([CH3:31])[C:22]=1[CH3:30])[O:19][C:18]([CH2:17][CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH:2]3[S:35][C:34](=[O:38])[NH:33][C:3]3=[O:4])=[CH:10][CH:11]=1)([CH3:32])[CH2:27][CH2:26]2

Participants

5

Reactant 3

HCID 31347SulfolaneHCID 2723790ThioureaHCID 20245699HCID 20245699, compound

Product 1

HCID 13488878HCID 13488878, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The procedure described in Example 1(a) was repeated, except that 13.5 g of ethyl 2-chloro-3-{4-[2-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)ethoxy]phenyl}propionate, 4.4 g of thiourea and 20 ml of sulfolane were reacted for 14 hours at 110° C. The crude product was dissolved in ethyl acetate and the solution was washed with water and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure and the resulting residue was purified by column chromatography through silica gel. This was first eluted with a 4:1 by volume mixture of benzene and ethyl acetate, and from these fractions were obtained the desired 5-{4-[2-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)ethoxy]benzyl}thiazolidine-2,4-dione, whose melting point and nuclear magnetic resonance spectra agreed with those of the product of Example 8.

Workup

  1. customwere reacted for 14 hours at 110° C
  2. washthe solution was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel
  6. washThis was first eluted with a 4:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-cda770944e48466f923ef3a7a3d8e42f
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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