Diglyme → HCID 178486136, compound

HRID 2423253Notes

Reaction equation

HRID 2423253 reaction equation
[CH3:1][N:2]([CH3:15])[S:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9](Cl)=[O:10])(=[O:5])=[O:4].[F:16][C:17]1[CH:18]=[C:19]([C:24](=[O:35])[CH:25]=[C:26]2[NH:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[NH:27]2)[CH:20]=[C:21]([F:23])[CH:22]=1.C(N(CC)CC)C.COCCOCCOC>O>[F:16][C:17]1[CH:18]=[C:19]([C:24](=[O:35])[C:25](=[C:26]2[NH:27][C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[NH:30]2)[C:9]([C:8]2[CH:7]=[C:6]([S:3]([N:2]([CH3:15])[CH3:1])(=[O:5])=[O:4])[CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:20]=[C:21]([F:23])[CH:22]=1

Participants

6

Reactant 4

HCID 8150DiglymeHCID 8471TriethylamineHCID 188018843-(Dimethylsulfamoyl)benzoyl chlorideHCID 1785203801-(3,5-difluorophenyl)-2-(1,3-dihydrobenzimidazol-2-ylidene)ethanone

Product 1

HCID 178486136HCID 178486136, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
110 °C

Procedure

3-[(dimethylamino)sulfonyl]benzoyl chloride (1.97 g) was added to a mixture of 1-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)ethanone (865 mg), triethylamine (1.6 mL) and 2-methoxyethyl ether (10 mL), followed by heating with stirring at 110° C. for 30 minutes. Water (0.06 mL) was added, followed by further heating under reflux for 30 minutes. After cooling, water was added, followed by extraction with ethyl acetate. The organic layer was washed with water, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1), and recrystallized from ethyl acetate/n-hexane to obtain 3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]-N,N-dimethylbenzenesulfonamide (391 mg).

Workup

  1. temperatureby heating
  2. temperatureby further heating
  3. temperatureunder reflux for 30 minutes
  4. temperatureAfter cooling
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)
  9. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-c15fb3922011467d92f05f3b699caebd
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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