Ethanol → HCID 13013930, compound

HRID 444146Notes

Reaction equation

HRID 444146 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:13]3[CH:14]=[CH:15][C:16]([C:18]([O:20]C)=[O:19])=[CH:17][C:12]=3[S:11][C:10]3[CH:22]=[CH:23][CH:24]=[CH:25][C:9]=3[N:8]=2)[CH2:3][CH2:2]1.[OH-].[K+].O.C(O)C>O1CCOCC1>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:13]3[CH:14]=[CH:15][C:16]([C:18]([OH:20])=[O:19])=[CH:17][C:12]=3[S:11][C:10]3[CH:22]=[CH:23][CH:24]=[CH:25][C:9]=3[N:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 13013931HCID 13013931, compound

Product 1

HCID 13013930HCID 13013930, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Stir a mixture of 1.77 gm. (5 mmole) of the ester of Example 11, 1.12 gm. (10 mmole) of 85% aqueous potassium hydroxide, 5.5 ml. of water, 27.5 ml. of ethanol and 2.75 ml. of dioxane under argon at room temperature for 21/2 hours. Evaporate to a small volume and dilute with 18 ml. of water. Filter and acidify with acetic acid to pH 4.5. Separate the precipitate by filtration, wash with water and dry in vacuo over calcium chloride. Recrystallize from acetonitrile to obtain the title product, (m.p. 267°-269° C.).

Workup

  1. additiona mixture of 1.77 gm
  2. customat room temperature
  3. custom2 hours
  4. customEvaporate to a small volume
  5. additiondilute with 18 ml
  6. filtrationFilter
  7. customSeparate the precipitate
  8. filtrationby filtration
  9. washwash with water
  10. dry with materialdry in vacuo over calcium chloride
  11. customRecrystallize from acetonitrile

Sources & evidence

ORD record
ord-05ae97fb40b14d79b3c617f670923405
Source dataset
uspto-grants-1981_04
Patent number
US04263207

Reaction notes

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