Acetic Acid → HCID 15295073, compound

HRID 1756691Notes

Reaction equation

HRID 1756691 reaction equation
C(O)(=O)C.[CH3:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:16])=[O:15])=[CH:9][CH:8]=1.[CH3:17][C:18]([CH3:36])([C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:27]=1[O:28][CH2:29][O:30][CH3:31])[CH2:23]N)[CH3:19]>C1(C)C=CC=CC=1>[CH3:35][C:32]([C:26]1[CH:25]=[C:22]([CH2:23][NH:16][C:14]([NH:13][C:10]2[CH:9]=[CH:8][C:7]([S:6][CH3:5])=[CH:12][CH:11]=2)=[O:15])[CH:21]=[C:20]([C:18]([CH3:36])([CH3:19])[CH3:17])[C:27]=1[O:28][CH2:29][O:30][CH3:31])([CH3:33])[CH3:34]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 306638N-[4-(Methylsulfanyl)phenyl]ureaHCID 19391054HCID 19391054, compound

Product 1

HCID 15295073HCID 15295073, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Acetic acid (1.08 g; 18 mmol), 4.5 g (24.7 mmol) of the compound of Example 5 and 5.0 g (18 mmol) of the compound of Example 1 were dissolved in 180 ml of toluene. The resulting solution was heated to reflux, stirred at that temperature for 4 hours and then cooled to room temperature. The cooled solution was washed with a IN hydrochloric acid solution, a saturated sodium bicarbonate solution, water and a saturated brine solution. The washed solution was then filtered to remove any solid particulates which had formed and the liltrate was concentrated to dryness to provide a residue. This residue was purified by column chromatography using a 20-40% ethyl acetate in hexane gradient as eluent. Fractions containing the above titled compound were combined and then concentrated to dryness to provide 3.14 g of title compound.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. washThe cooled solution was washed with a IN hydrochloric acid solution
  4. filtrationThe washed solution was then filtered
  5. customto remove any solid particulates which
  6. customhad formed
  7. concentrationthe liltrate was concentrated to dryness
  8. customto provide a residue
  9. customThis residue was purified by column chromatography
  10. additionFractions containing the above titled compound
  11. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fb923c617bfe4b63a8c577f4cb4c064d
Source dataset
uspto-grants-1995_08
Patent number
US05441984

Reaction notes

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