Hydrochloric Acid → HCID 13605836, compound

HRID 1589694Notes

Reaction equation

HRID 1589694 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[C:15]([CH3:18])([CH3:17])[CH3:16])[O:11][C:10]([CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH:29](Cl)[C:30](OCC)=[O:31])=[CH:24][CH:23]=1)([CH3:19])[CH2:9][C:8]2=[O:36])(=O)C.[NH2:37][C:38](N)=[S:39].S1(CCCC1)(=O)=[O:42].Cl>C(OCC)(=O)C.O.COCCO>[C:15]([C:14]1[CH:13]=[C:12]2[C:7]([C:8](=[O:36])[CH2:9][C:10]([CH2:20][O:21][C:22]3[CH:23]=[CH:24][C:25]([CH2:28][CH:29]4[S:39][C:38](=[O:42])[NH:37][C:30]4=[O:31])=[CH:26][CH:27]=3)([CH3:19])[O:11]2)=[CH:6][C:5]=1[OH:4])([CH3:18])([CH3:16])[CH3:17]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 31347SulfolaneHCID 2723790ThioureaHCID 20245643HCID 20245643, compound

Product 1

HCID 13605836HCID 13605836, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80192-MethoxyethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a similar manner to Example 22, a mixture of 291 mg of ethyl 3-[4-(6-acetoxy-7-t-butyl-2-methyl-4-oxochroman-2-ylmethoxy)phenyl]-2-chloropropionate (prepared as described in Preparation 49), 64 mg of thiourea and 1 ml of sulfolane was heated. 5 ml of ethylene glycol monomethyl ether, 1 ml of concentrated hydrochloric acid and 2 ml of water were added, and the resulting mixture was further heated under reflux for 6 hours. Ethyl acetate was then added to the reaction mixture, and the resulting solution was washed with water and dried over anhydrous sodium sulfate. The ethyl acetate was removed by evaporation under reduced pressure, and the resulting residue was subjected to silica gel column chromatography, eluted with a 5:1 by volume mixture of benzene and ethyl acetate, to give 143 mg of the desired 5-[4-(7-t-butyl-6-hydroxy-2-methyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione.

Workup

  1. temperaturewas heated
  2. temperaturethe resulting mixture was further heated
  3. temperatureunder reflux for 6 hours
  4. washthe resulting solution was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe ethyl acetate was removed by evaporation under reduced pressure
  7. washeluted with a 5:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-e372153c9a154cdd84440f311dea3f33
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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