Butyl ether → HCID 86733632, compound

HRID 1659105Notes

Reaction equation

HRID 1659105 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[CH2:10][S:9][C:8]2=[S:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([O:18][CH2:19][CH2:20]CC)[CH2:15][CH2:16][CH3:17]>>[CH2:19]([O:18][C:14](=[C:10]1[S:9][C:8](=[S:13])[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:11]1=[O:12])[CH2:15][C:16]1[CH:17]=[CH:3][CH:2]=[CH:1][CH:6]=1)[CH3:20]

Participants

3

Reactant 2

HCID 8909Butyl etherHCID 738224-Thiazolidinone, 3-phenyl-2-thioxo-

Product 1

HCID 86733632HCID 86733632, compound

Procedure

Alternatively, a mixture of 6 g. (0.029 m.) of 3-phenyl-rhodanine, 15 g. (0.063 m.) of triethylorthophenylacetate and 15 ml. of n-butyl ether is heated to reflux and then distillate is removed until the temperature of the mixture reaches 150°C. After heating at this temperature for one hour, an additional 5 g. of orthoester is added and heating is continued for 30 minutes. To the reaction mixture is added 5 ml. of acetic anhydride and heating is continued for 5 minutes. The resulting mixture is concentrated in vacuo and the residue is eluted through a column of silica gel with 2:1-cyclohexane-benzene. The product from the first eluates give 5-(1'-ethoxy-2'-phenylethylidene)-3-phenylrhodanine, m.p. 119°-121°C. Alkaline hydrolysis as described above of this intermediate furnishes the identical hydroxy derivative.

Workup

  1. additionAlternatively, a mixture of 6 g
  2. temperatureto reflux
  3. customdistillate is removed until the temperature of the mixture
  4. customreaches 150°C
  5. temperatureAfter heating at this temperature for one hour
  6. additionof orthoester is added
  7. temperatureheating
  8. additionTo the reaction mixture is added 5 ml
  9. temperatureof acetic anhydride and heating
  10. waitis continued for 5 minutes
  11. concentrationThe resulting mixture is concentrated in vacuo
  12. washthe residue is eluted through a column of silica gel with 2

Sources & evidence

ORD record
ord-b0610f7766c84f4fafb71016064890a4
Source dataset
uspto-grants-1976_06
Patent number
US03966942

Reaction notes

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