Morpholine → HCID 10331103, compound

HRID 733307Notes

Reaction equation

HRID 733307 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH3:12])=[C:7]([O:14]C)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[S].[NH:17]1[CH2:22]COC[CH2:18]1>O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][N:17]([CH3:22])[CH3:18])=[C:7]([OH:14])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5362487SulfurHCID 68717015HCID 68717015, compound

Product 1

HCID 10331103HCID 10331103, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 5.76 g (27.9 mmol) of 1-(4-tert-butyl-2-methoxyphenyl)ethanone (described in patent applications WO 01/02366; WO 99/52857; WO 99/21836; WO 97/48683), 1.1 g (34.3 mmol) sulfur and 15 mL morpholine (0.172 mol) was refluxed overnight under a nitrogen atmosphere. The reaction mixture was cooled and poured into 200 mL water containing 30 g sodium hydroxide and the resulting mixture was again refluxed overnight. The reaction mixture was then cooled to room temperature, diluted with an equal volume of water, and filtered through a pad of Celite filter aid. The filtrate was then cooled with an external ice water bath and acidified. The resulting precipitate was filtered, washed with water and air dried. The residue was then suspended in EtOAc and filtered to remove insoluble material and the filtrate was concentrated in vacuo to afford the title compound.

Workup

  1. temperaturewas refluxed overnight under a nitrogen atmosphere
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through a pad of Celite
  4. filtrationfilter aid
  5. temperatureThe filtrate was then cooled with an external ice water bath
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with water and air
  8. customdried
  9. filtrationfiltered
  10. customto remove insoluble material
  11. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fdd56f07c56f47fdaecef657b869d2ef
Source dataset
uspto-grants-2009_09
Patent number
US07589127B2

Reaction notes

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