Hydrochloric Acid → HCID 14501227, compound

HRID 1198899Notes

Reaction equation

HRID 1198899 reaction equation
[CH3:1]I.[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[C:9](=[O:14])[NH:10][CH2:11][CH2:12][N:13]=1.O.Cl>C(OCC)C.O1CCCC1>[CH3:1][C:8]1([C:4]2[S:3][CH:7]=[CH:6][CH:5]=2)[NH:13][CH2:12][CH2:11][NH:10][C:9]1=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6328Methyl iodideHCID 14501226HCID 14501226, compound

Product 1

HCID 14501227HCID 14501227, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The Grignard solution prepared from 7.3 g of Mg and 42.6 g of methyl iodide in 150 ml of diethyl ether is added dropwise slowly at room temperature to a solution of 18 g of 3-(thien-2-yl)-5,6-dihydropyrazin-2-one in 150 ml of tetrahydrofuran. Stirring is continued for 15 hours at room temperature and the mixture is then hydrolyzed with 100 ml of water. The pH of the mixture is adjusted to 2 with concentrated HCl, the organic phase is separated off and the aqueous phase is extracted twice by shaking with diethyl ether and its pH is adjusted to 8 with potassium carbonate. The compound is then extracted with methylene chloride. The methylene chloride phase is dried and concentrated. The residual oil is purified by column chromatography over silica gel made by Merck, Darmstadt, type "0.04-0.06", the mobile phase being methylene chloride/methanol in a ratio by volume of 95:5. The fractions containing the compound are concentrated on a rotary evaporator and the residue is recrystallized from isopropanol.

Workup

  1. customthe organic phase is separated off
  2. extractionthe aqueous phase is extracted twice
  3. stirringby shaking with diethyl ether and its pH
  4. extractionThe compound is then extracted with methylene chloride
  5. dry with materialThe methylene chloride phase is dried
  6. concentrationconcentrated
  7. customThe residual oil is purified by column chromatography over silica gel
  8. additionThe fractions containing the compound
  9. concentrationare concentrated on a rotary evaporator
  10. customthe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-6adc19b330154ff59ff48552d0f2b461
Source dataset
uspto-grants-1990_02
Patent number
US04898866

Reaction notes

Loading…