Water → HCID 68717218, compound
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH3:12])=[C:7]([O:14][CH3:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[S].N1CC[O:20]CC1.[OH2:23]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:20])=[O:23])=[C:7]([O:14][CH3:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]Participants
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
- temperaturewas refluxed overnight under a nitrogen atmosphere
- temperatureThe reaction mixture was cooled
- filtrationfiltered through a pad of Celite
- filtrationfilter aid
- temperatureThe filtrate was then cooled with an external ice water bath
- filtrationThe resulting precipitate was filtered
- washwashed with water and air
- customdried
- filtrationfiltered
- customto remove insoluble material
- concentrationthe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-80fa619edfc24191beab8c547760ce8a
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834062B2
Reaction notes
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