Ethanol → HCID 13013928, compound

HRID 444144Notes

Reaction equation

HRID 444144 reaction equation
[CH:1]1[C:6]2[CH:7]=[N:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][C:5]=2[CH:4]=[C:3]([C:16]([O:18]C)=[O:17])[CH:2]=1.[OH-].[K+].C(O)C.O1CCOCC1>O>[CH:1]1[C:6]2[CH:7]=[N:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][C:5]=2[CH:4]=[C:3]([C:16]([OH:18])=[O:17])[CH:2]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 13013929HCID 13013929, compound

Product 1

HCID 13013928HCID 13013928, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 269 mg. (1 mmole) of the ester of Example 9 to a solution of 132 mg. (2 mmole) of 85% aqueous potassium hydroxide in a mixture of 6.5 ml. of ethanol, 0.65 ml. of dioxane and 1.3 ml. of water. Stir at room temperature for 2 hours. Filter and evaporate the solution to a small volume. Dilute with 9 ml. of water and acidify with acetic acid. Filter wash the solids with water and dry. Dissolve the product in 9 ml. of hot tetrahydrofuran, filter and dilute with 9 ml. of methanol. Evaporate to a thick slurry, dilute with 2 ml. of methanol, filter and wash with methanol. Dry to obtain the title product, (m.p. sinters 289° C., m.p. 290°-291° C. dec.).

Workup

  1. additionAdd 269 mg
  2. filtrationFilter
  3. customevaporate the solution to a small volume
  4. additionDilute with 9 ml
  5. filtrationFilter
  6. washwash the solids with water
  7. customdry
  8. dissolutionDissolve the product in 9 ml
  9. filtrationof hot tetrahydrofuran, filter
  10. additiondilute with 9 ml
  11. customEvaporate to a thick slurry
  12. additiondilute with 2 ml
  13. filtrationof methanol, filter
  14. washwash with methanol
  15. customDry

Sources & evidence

ORD record
ord-7a0742a4c3b7411d918aa9c9246750fb
Source dataset
uspto-grants-1981_04
Patent number
US04263207

Reaction notes

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