Water → HCID 21832206, compound

HRID 1901150Notes

Reaction equation

HRID 1901150 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[OH:4].O=[C:13]([CH3:30])[CH2:14][O:15][C:16]1[CH:29]=[CH:28][C:19]([CH2:20][CH:21]2[S:25][C:24](=[O:26])[NH:23][C:22]2=[O:27])=[CH:18][CH:17]=1.O>C1C=CC=CC=1>[Cl:11][C:7]1[CH:6]=[C:5]([CH:3]([OH:4])[CH2:2][NH:1][CH:13]([CH3:30])[CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:20][CH:21]3[S:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])=[CH:28][CH:29]=2)[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 218321505-[4-(2-Oxopropoxy)benzyl]thiazolidine-2,4-dione

Product 1

HCID 21832206HCID 21832206, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2.5 g of 2-amino-1-(3-chlorophenyl)ethanol (prepared as described in Preparation 8) and 3.58 g of 5-[4-(2-oxopropoxy)benzyl]thiazolidine -2,4-dione in 50 ml of benzene was heated under reflux for 1.5 hours, whilst the water being formed during the reaction was continuously removed. At the end of this time, the benzene used was removed by distillation under reduced pressure. The resulting residue was dissolved in 100 ml of absolute methanol, and then 3 g of sodium borohydride were added to the resulting solution. The reaction mixture was allowed to stand overnight at room temperature, after which it was concentrated by evaporation under reduced pressure, and the concentrate was mixed with water. The resulting aqueous mixture was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using ethyl acetate, followed by a 10:1 by volume mixture of ethyl acetate and ethanol, as the eluent. The product was recrystallized from ethyl acetate, to give 0.74 g of the title compound as crystals, melting at 100°-125° C.

Workup

  1. customformed during the reaction
  2. customwas continuously removed
  3. customAt the end of this time, the benzene used was removed by distillation under reduced pressure
  4. dissolutionThe resulting residue was dissolved in 100 ml of absolute methanol
  5. addition3 g of sodium borohydride were added to the resulting solution
  6. concentrationafter which it was concentrated by evaporation under reduced pressure
  7. additionthe concentrate was mixed with water
  8. extractionThe resulting aqueous mixture was extracted with ethyl acetate
  9. dry with materialthe extract was dried over anhydrous sodium sulfate
  10. customThe solvent was removed by distillation under reduced pressure
  11. customthe resulting residue was purified by column chromatography through silica gel
  12. additionfollowed by a 10:1 by volume mixture of ethyl acetate and ethanol, as the eluent
  13. customThe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-32941cdd5c6c45caadc676eae8b8b188
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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