Acetic Acid → HCID 10015485, compound

HRID 1089979Notes

Reaction equation

HRID 1089979 reaction equation
C(O[C:4]1[CH:8]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18]C)=[CH:13][CH:12]=2)[CH2:7][CH2:6][N:5]=1)C.CO[CH:22](OC)[CH2:23][NH2:24].C(O)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C.C1C=CC=CC=1>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][S:9][CH:8]2[C:4]3=[N:24][CH:23]=[CH:22][N:5]3[CH2:6][CH2:7]2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 89728Aminoacetaldehyde dimethyl acetalHCID 19978608HCID 19978608, compound

Product 1

HCID 10015485HCID 10015485, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

2-Ethoxy-3-p-ethoxybenzylthio-1-pyrroline (531mg) (synthesized according to the method disclosed in Japanese Patent Laid-Open No. 56987/1985), aminoacetaldehyde dimethylacetal (315mg) and acetic acid (180mg) were dissolved in 30 ml of ethanol and refluxed under heating for one hour. The reaction solution was evaporated to dryness in vacuo, the residue was distributed between benzene and 40 ml of water containing 4 ml of 1N sodium hydroxide aqueous solution, the benzene phase was washed with water and dried over MgSO4 and thereafter the solvent was distilled off in vacuo to obtain 700mg of colorless and transparent material. The oily material was dissolved in 30 ml of benzene, 1.14 g of p-toluenesulfonic acid (hydrate) was added thereto and refluxed under heating for one hour. The reaction solution was cooled, washed with 5% aqueous solution of sodium bicarbonate and water and dried, then the solvent was distilled off. The residue was purified by column chromatography using a column packed with 20 g of silica gel (eluent: Chloroform/methanol (19:1 v/v)) to obtain the objective compound as a colorless and transparent oil. The compound was crystallized during standing in a refrigerator (m.p.=65°~73° C.; yield: 0.53 g).

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for one hour
  3. customThe reaction solution was evaporated to dryness in vacuo
  4. washthe benzene phase was washed with water
  5. dry with materialdried over MgSO4
  6. distillationthe solvent was distilled off in vacuo
  7. customto obtain 700mg of colorless and transparent material
  8. temperaturerefluxed
  9. temperatureunder heating for one hour
  10. temperatureThe reaction solution was cooled
  11. washwashed with 5% aqueous solution of sodium bicarbonate and water
  12. customdried
  13. distillationthe solvent was distilled off
  14. customThe residue was purified by column chromatography
  15. customto obtain the objective compound as a colorless and transparent oil
  16. customThe compound was crystallized

Sources & evidence

ORD record
ord-e5f83fe4dab348febd6fb4ba1619435c
Source dataset
uspto-grants-1992_01
Patent number
US05079357

Reaction notes

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