Cesium carbonate → HCID 178512580, compound

HRID 1715687Notes

Reaction equation

HRID 1715687 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)(O)O.[NH2:27][C:28]([NH2:30])=[NH:29]>CN1CCCC1=O.CCOCC>[N:11]1([S:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:29][C:28]([NH2:30])=[NH:27])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 286947Carbonic acid-guanidine (1:1)HCID 7553774-((4-Fluorophenyl)sulfonyl)morpholine

Product 1

HCID 178512580HCID 178512580, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
87.5 °C

Procedure

A mixture of 4-[(4-fluorophenyl)sulfonyl]morpholine (0.25 g, 1 mmol), cesium carbonate (1.30 g, 4 mmol), and guanidine carbonate (1.08 g, 6 mmol) in 2 ml of 1-methyl-2-pyrrolidinone (NMP) is stirred at 85 to 90° C. for 24 hrs. It is then cooled to room temperature and diluted with ether. The resulting suspension is filtered, and the precipitate extracted with tetrahydrofuran (THF) to yield, after evaporation of solvent, 0.12 g of a yellow solid; mp 102-105° C.; MS (ESI) m/z 285.1 (M+H); HRMS: calcd for C11H16N4O3S, 284.0943; found (ESI_FT), 285.1011 (M+H).

Workup

  1. temperatureIt is then cooled to room temperature
  2. filtrationThe resulting suspension is filtered
  3. extractionthe precipitate extracted with tetrahydrofuran (THF)
  4. customto yield
  5. customafter evaporation of solvent, 0.12 g of a yellow solid

Sources & evidence

ORD record
ord-ac36ebab31a040efb39b4cceaaa0c710
Source dataset
uspto-grants-2010_09
Patent number
US07799915B2

Reaction notes

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