Water → AL 321

HRID 326158Notes

Reaction equation

HRID 326158 reaction equation
[CH3:1][C:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:21])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([S:18][C:19]#[N:20])[C:13](OCC)=[O:14])=[CH:7][CH:6]=1.[OH2:28]>C(O)C.Cl>[CH3:21][C:2]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([CH3:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]2[S:18][C:19](=[O:28])[NH:20][C:13]2=[O:14])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 962WaterHCID 12830988HCID 12830988, compound

Product 1

HCID 194620AL 321

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

1.9 g Of ethyl 3-[4-(2-methyl-2-phenylpropyloxy)phenyl]-2-thiocyanatopropionate is dissolved in 20 ml of ethanol and to the solution 20 ml of 6 N-hydrochloric acid is added. The mixture is refluxed for 24 hours. After cooling, water is added to the mixture. The mixture is subjected to extraction with ether. The extract is washed with water and then dried. After distilling off ether, the residure is crystallized from ether-n-hexane, whereby 730 mg of 5-[4-(2-methyl-2-phenylpropyloxy)benzyl]thiazolidine-2,4-dione is obtained.

Workup

  1. additionis added
  2. temperatureThe mixture is refluxed for 24 hours
  3. temperatureAfter cooling
  4. extractionThe mixture is subjected to extraction with ether
  5. washThe extract is washed with water
  6. customdried
  7. distillationAfter distilling off ether
  8. customthe residure is crystallized from ether-n-hexane

Sources & evidence

ORD record
ord-a86b4cd079d544eb80fcd767e2c89459
Source dataset
uspto-grants-1984_04
Patent number
US04444779

Reaction notes

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