Hydrochloric Acid → 5-[4-(2-Methylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

HRID 2351499Notes

Reaction equation

HRID 2351499 reaction equation
Cl[CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2([CH3:27])[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[O:18]2)=[CH:11][CH:10]=1)[C:3](OCC)=[O:4].[NH2:28][C:29](N)=[S:30].S1(CCCC1)(=O)=[O:33].Cl>O.COCCO>[CH3:27][C:17]1([CH2:16][O:15][C:12]2[CH:11]=[CH:10][C:9]([CH2:8][CH:2]3[S:30][C:29](=[O:33])[NH:28][C:3]3=[O:4])=[CH:14][CH:13]=2)[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[O:18]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31347SulfolaneHCID 2723790ThioureaHCID 15613914Ethyl 2-chloro-3-[4-(2-methylchroman-2-ylmethoxy)phenyl]propionate

Product 1

HCID 109378505-[4-(2-Methylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 330 mg of ethyl 2-chloro-3-[4-(2-methylchroman-2-ylmethoxy)phenyl]propionate (prepared as described in Preparation 5), 100 mg of thiourea and 1 ml of sulfolane was heated at 130° C. for 5 hours. At the end of this time, 2 ml of ethylene glycol monomethyl ether and 1.5 ml of 2N aqueous hydrochloric acid were added to the reaction mixture, which was then heated under reflux for 4.5 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography eluted with a 2:1 by volume mixture of hexane and ethyl acetate. The oily substance thereby obtained was washed with warm water and dried, to give 230 mg of the title compound as a pale yellow glass, softening at 42°-50° C.

Workup

  1. temperaturewas then heated
  2. temperatureunder reflux for 4.5 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. washeluted with a 2:1 by volume mixture of hexane and ethyl acetate
  7. customThe oily substance thereby obtained
  8. washwas washed with warm water
  9. customdried

Sources & evidence

ORD record
ord-170781da010e4a559d522173a4c8b940
Source dataset
uspto-grants-1989_10
Patent number
US04873255

Reaction notes

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