Hydrochloric Acid → 4(1H)-Pyrimidinone, 3-(2,6-dimethylphenyl)-1-ethyltetrahydro-2-thioxo-

HRID 2393328Notes

Reaction equation

HRID 2393328 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[S:19])[N:11]([CH2:14][CH2:15][C:16](O)=[O:17])[CH2:12][CH3:13].Cl>CC(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[C:16](=[O:17])[CH2:15][CH2:14][N:11]([CH2:12][CH3:13])[C:10]1=[S:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18975625HCID 18975625, compound

Product 1

HCID 113115614(1H)-Pyrimidinone, 3-(2,6-dimethylphenyl)-1-ethyltetrahydro-2-thioxo-Yield 47.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-[3-(2,6-dimethylphenyl)-1-ethyl-thioureido]propionic acid (12 g) was dissolved in acetone (245 mL). Conc. HCl (5 mL) was added and the mixture was heated at reflux for 18 hours. The reaction mixture was evaporated to dryness. The residue was dissolved in methylene chloride (100 mL), and washed with 1N NaOH. The organic phase was dried over anhydrous magnesium sulfate, then evaporated to dryness. The solid was recrystallized from ethyl acetate to give the title compound (5.3 g) as a white solid, m.p. 124°-126° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 18 hours
  3. customThe reaction mixture was evaporated to dryness
  4. dissolutionThe residue was dissolved in methylene chloride (100 mL)
  5. washwashed with 1N NaOH
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  7. customevaporated to dryness
  8. customThe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-04600c432d684dc08cc38c7b1c728ebe
Source dataset
uspto-grants-1998_09
Patent number
US05807864

Reaction notes

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