Methanol → HCID 18376321, compound

HRID 2300591Notes

Reaction equation

HRID 2300591 reaction equation
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:11]([CH2:20][CH3:21])[C:12](=O)[CH2:13][C:14]([O:16]CC)=[O:15].O.CO>C1(C)C=CC=CC=1>[CH2:20]([C:11]1[S:8][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:9][C:12]=1[CH2:13][C:14]([OH:16])=[O:15])[CH3:21]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 683563ThiobenzamideHCID 1278044452851-15-7

Product 1

HCID 18376321HCID 18376321, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 8.7 g (63.3 mmol) of thiobenzamide and 10 g (42.2 mmol) of ethyl 4-bromo-3-oxo-hexanoate in 45 mL of toluene was refluxed for 6 hrs with Dean-Stark trap removal of water. Cooled, added methanol, and continued reflux for 1 h. Cooled, partially concentrated (˜½ volume), then 30 mL of 2.0 M NaOH solution was added. Stirred the mixture at 80° C. for 2 hrs before cooling and extraction of the aqueous with EtOAc. The aqueous phase was treated with 70 mL of 1.0 M citric acid with heating (70° C.) for 45 min. The mixture was extracted with EtOAc, and the extracts were dried. over MgSO4, filtered and concentrated to yield a yellow colored solid upon standing at ambient temperature (8.4 g, ˜80% yield); 1H NMR (CDCl3, 300 MHz) δ7.95-7.87 (m, 2H), 7.48-7.45 (m, 3H), 3.86 (s, 2H), 2.85 (q, 2H, J=7.5), 1.36 (t, 3H, J=7.5).

Workup

  1. temperatureCooled
  2. temperaturecontinued reflux for 1 h
  3. temperatureCooled
  4. concentrationpartially concentrated (˜½ volume)
  5. addition30 mL of 2.0 M NaOH solution was added
  6. temperaturebefore cooling
  7. extractionextraction of the aqueous with EtOAc
  8. additionThe aqueous phase was treated with 70 mL of 1.0 M citric acid
  9. temperaturewith heating (70° C.) for 45 min
  10. extractionThe mixture was extracted with EtOAc
  11. customthe extracts were dried
  12. filtrationover MgSO4, filtered
  13. concentrationconcentrated
  14. customto yield a yellow colored solid
  15. customupon standing at ambient temperature

Sources & evidence

ORD record
ord-bfc0336e912542c79dc9b0930bc47a00
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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