Hydrochloric Acid → 5-[4-(6-Hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

HRID 1589692Notes

Reaction equation

HRID 1589692 reaction equation
C([O:4][C:5]1[C:6]([CH3:35])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH:27](Cl)[C:28](OCC)=[O:29])=[CH:22][CH:21]=1)([CH3:17])[CH2:9][C:8]2=[O:34])(=O)C.[NH2:36][C:37](N)=[S:38].S1(CCCC1)(=O)=[O:41].Cl>O.COCCO>[OH:4][C:5]1[C:6]([CH3:35])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH:27]3[S:38][C:37](=[O:41])[NH:36][C:28]3=[O:29])=[CH:24][CH:25]=1)([CH3:17])[CH2:9][C:8]2=[O:34]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31347SulfolaneHCID 2723790ThioureaHCID 13649224Ethyl 3-[4-(6-acetoxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)phenyl]-2-chloropropionate

Product 1

HCID 98252415-[4-(6-Hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 1.3 g of ethyl 3-[4-(6-acetoxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)phenyl]-2-chloropropionate (prepared as described in Preparation 45), 0.4 g of thiourea and 2 g of sulfolane was heated at 120°-130° C. for 4 hours under a nitrogen stream. Then 15 ml of ethylene glycol monomethyl ether, 4 ml of water and 2 ml of concentrated hydrochloric acid were added, in that order, to the reaction mixture, and heating was continued, but at 70°-90° C., for a further 2.5 days. Water was then added to the reaction mixture, after which it was extracted with benzene. The extract was washed with water and dried over anhydrous sodium sulfate. Benzene was distilled off from the extract. The residue was subjected to silica gel column chromatography, eluted with a 5:3 by volume mixture of hexane and ethyl acetate, to yield 5-[4-(6-hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione. Its softening point was 79°-83° C.

Workup

  1. temperaturewas heated at 120°-130° C. for 4 hours under a nitrogen stream
  2. temperatureheating
  3. extractionafter which it was extracted with benzene
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationBenzene was distilled off from the extract
  7. washeluted with a 5:3 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-3ae1d1321d824867b0f0aaa1c6bb3cb8
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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