Hydrochloric Acid → HCID 178458839, compound

HRID 2291236Notes

Reaction equation

HRID 2291236 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[C:10]([CH2:16][C:17]#[N:18])[C:9]=2[CH3:19])[CH2:5][C:4](=[O:20])[C:3]=1[C:21](=[O:24])[CH2:22][CH3:23].C(N)(=[S:27])C.Cl>>[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[C:10]([CH2:16][C:17](=[S:27])[NH2:18])[C:9]=2[CH3:19])[CH2:5][C:4](=[O:20])[C:3]=1[C:21](=[O:24])[CH2:22][CH3:23]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 2723949ThioacetamideHCID 178458837HCID 178458837, compound

Product 1

HCID 178458839HCID 178458839, compound

Procedure

A solution of 3-hydroxy-2-propionyl-5-(3-cyanomethyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (0.77 g, 2.37 mmol) and thioacetamide (0.36 g, 4.74 mmol) in dmf (10 ml) was saturated with anhydrous hydrogen chloride. The solutuion was then heated under a distillation head at 110° for 45 m. Most of the dmf was then distilled off under reduced pressure. The dark red residue was cooled, saturated sodium bicarbonate solution was added, and the aqueous layer extracted with ethylacetate. The organic layer was washed extensively with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield an orange solid. The crude material was purified by chromatography on silica gel (elution with an increasing gradient of ethylacetate in methylene chloride) to give 3-hydroxy-2-propionyl-5-(3-thiocarbamoylmethyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one as a colourless solid (0.40, 47%). Proton magnetic resonance spectrum (CDCl3 ; δ in ppm); 1.15 (3H, t); 2.22 (3H,s); 2.28 (3H,s); 2.36 (3H,s); 2.4-4.2 (9H,m); 6.70 (1H,brs); 6.90 (1H,s); 8.25 (1H,brs); 18.20 (1H,s).

Workup

  1. temperatureThe solutuion was then heated under a distillation head at 110° for 45 m
  2. distillationMost of the dmf was then distilled off under reduced pressure
  3. temperatureThe dark red residue was cooled
  4. additionsaturated sodium bicarbonate solution was added
  5. extractionthe aqueous layer extracted with ethylacetate
  6. washThe organic layer was washed extensively with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto yield an orange solid
  10. customThe crude material was purified by chromatography on silica gel (
  11. washelution with an increasing gradient of ethylacetate in methylene chloride)

Sources & evidence

ORD record
ord-952ebc60d1694115b99646d969e4ff6e
Source dataset
uspto-grants-1989_01
Patent number
US04795487

Reaction notes

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