Potassium Carbonate → HCID 68285843, compound

HRID 1518683Notes

Reaction equation

HRID 1518683 reaction equation
[CH3:1][N:2]([CH3:26])[CH:3]=[N:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[CH:15]([CH3:24])[C:16]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[S:17])=[CH:10][CH:9]=1)(=[O:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].I[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>CC(C)=O>[CH2:38]([O:37][C:35]([C:34]1[S:17][C:16]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:15]([CH3:24])[C:14]=1[C:11]1[CH:12]=[CH:13][C:8]([S:5](=[O:7])(=[O:6])[N:4]=[CH:3][N:2]([CH3:26])[CH3:1])=[CH:9][CH:10]=1)=[O:36])[CH3:39]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12183Ethyl iodoacetateHCID 86705023HCID 86705023, compound2×

Product 1

HCID 68285843HCID 68285843, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
57.5 °C

Procedure

To a stirred solution of N,N-dimethyl-N′-((4-(2-methyl-3-morpholino-3-thioxopropanoyl)phenyl)sulfonyl)formimidamide (compound 24c, 0.180 g, 0.45 mmol) in dry acetone (15 ml) was added potassium carbonate (0.45 g, 3.17 mmol) at room temperature. The resulting mixture was stirred at 55-60° C. for 2 hr. The reaction mixture was cooled to 0° C. and to this was added ethyl iodoacetate (0.097 g, 0.053 ml, 0.45 mmol) in a dropwise manner. The reaction mixture was stirred at reflux temperature for 4 hr. The progress of the reaction was monitored by TLC. The reaction mixture was allowed to warm to room temperature and filtered through a celite pad. The celite pad was washed with acetone (2×10 ml). The filtrate was concentrated under reduced pressure to obtain a crude product, which was purified by column chromatography over silica gel (100-200 mesh) using 50-55% ethyl acetate in hexanes as an eluent to obtain the title compound (0.091 g, 43%)

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringThe reaction mixture was stirred
  3. temperatureat reflux temperature for 4 hr
  4. temperatureto warm to room temperature
  5. filtrationfiltered through a celite pad
  6. washThe celite pad was washed with acetone (2×10 ml)
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto obtain a crude product, which
  9. customwas purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-0bbfb7a0d3a74c4085cf93a5f258e650
Source dataset
uspto-grants-2015_07
Patent number
US09072731B2

Reaction notes

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