Ethanol → HCID 13013943, compound

HRID 444142Notes

Reaction equation

HRID 444142 reaction equation
[CH:1]1[C:6]2[CH2:7][NH: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+].O.C(O)C>O1CCOCC1>[CH:1]1[C:6]2[CH2:7][NH: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 962WaterHCID 14797Potassium HydroxideHCID 13013927HCID 13013927, compound

Product 1

HCID 13013943HCID 13013943, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Stir a mixture of 136 mg. (0.5 mmole) of the ester of Example 7, 65.9 mg. (1 mmole) of 85% aqueous potassium hydroxide, 0.65 ml. of water, 3.25 ml. of ethanol, and 0.325 ml. of dioxane under argon at room temperature for 12 hours. Evaporate the mixture to dryness. Dissolve the residue in water and acidify with acetic acid. Recover the precipitate by filtration and wash with water. Dry in vacuo over calcium chloride and recrystallize from acetonitrile to obtain the title product (sinters and darkens at 237° C., m.p. 243° C. dec.).

Workup

  1. additiona mixture of 136 mg
  2. customEvaporate the mixture to dryness
  3. dissolutionDissolve the residue in water
  4. customRecover the precipitate
  5. filtrationby filtration
  6. washwash with water
  7. dry with materialDry in vacuo over calcium chloride
  8. customrecrystallize from acetonitrile

Sources & evidence

ORD record
ord-5d91d773549b4c95ad8af12d7bed672d
Source dataset
uspto-grants-1981_04
Patent number
US04263207

Reaction notes

Loading…