4-Methylmorpholine → HCID 59140422, compound

HRID 216349Notes

Reaction equation

HRID 216349 reaction equation
CN1CCOCC1.[CH3:8][C:9]([CH3:18])([CH2:16][CH3:17])[CH2:10][C:11]1[N:12]=[CH:13][NH:14][CH:15]=1.[CH3:19][N:20]([CH3:25])[S:21](Cl)(=[O:23])=[O:22]>C(COC)OC>[CH3:8][C:9]([CH3:18])([CH2:16][CH3:17])[CH2:10][C:11]1[N:12]=[CH:13][N:14]([S:21]([N:20]([CH3:25])[CH3:19])(=[O:23])=[O:22])[CH:15]=1

Participants

5

Reactant 3

HCID 79724-Methylmorpholine2×HCID 83372Dimethylsulphamoyl chloride2×HCID 178442466HCID 178442466, compound

Product 1

HCID 59140422HCID 59140422, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
40 °C

Procedure

N-methylmorpholine (54 mL, 0.48 mol) was added to a solution of 4-(2,2-dimethylbutyl)-1H-imidazole (36 g, 0.24 mol) in dimethoxyethane (360 mL). After warming to 40° C., N,N-dimethylsulfamoyl chloride (38 mL, 0.36 mol) was added over 15 min. After stirring at 40° C. for 2 h, N-methylmorpholine (11 mL) and N,N-dimethylsulfamoyl chloride (8 mL) were added. After stirring for an additional 2 h, and the reaction mixture was cooled and filtered rinsing with ether. The filtrate was extracted with ether. The combined organic extracts were washed with brine, dried (magnesium sulfate), filtered, concentrated in vacuo. Chromatography over silica afforded the title compound.

Workup

  1. stirringAfter stirring for an additional 2 h
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered
  4. washrinsing with ether
  5. extractionThe filtrate was extracted with ether
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ff13b0224cd43ceb43ff511841512ed
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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