Water → HCID 18518328, compound

HRID 1369227Notes

Reaction equation

HRID 1369227 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](N2CCOCC2)=S)=[C:5]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:4]=1.[OH-:25].[K+].[OH2:27]>CC(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:27])=[O:25])=[C:5]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 18518304HCID 18518304, compound

Product 1

HCID 18518328HCID 18518328, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 2-(4-methoxy-2-phenoxyphenyl)-1-morpholin-4-ylethan-1-thione (0.35 g, 1.02 mmole) in i-PrOH (15 mL) and H2O (15 mL) was added KOH (0.57 g, 10.2 mmole). The reaction was heated at reflux for 18 hr, then was cooled to RT, diluted with H2O, and washed with Et2O. The aqueous layer was acidified to pH≈4 with conc. HCl and was extracted with CHCl3. The combined extracts were dried over MgSO4 and concentrated to give the title compound (0.22 g) as a white solid. This was used without further purification: MS (ES) m/e 259.0 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 hr
  3. washwashed with Et2O
  4. extractionwas extracted with CHCl3
  5. dry with materialThe combined extracts were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-726d124057cc447aac688632ca024f3f
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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