Cesium carbonate → HCID 57898798, compound

HRID 217281Notes

Reaction equation

HRID 217281 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:7][C:8]1[N:13]=[C:12]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=[C:10]([C:22]2[C:23]([Cl:30])=[CH:24][C:25]([Cl:29])=[C:26]([OH:28])[CH:27]=2)[N:9]=1.Br[CH2:32][C:33]#[N:34]>CN(C)C=O>[NH2:7][C:8]1[N:13]=[C:12]([S:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:11]=[C:10]([C:22]2[C:23]([Cl:30])=[CH:24][C:25]([Cl:29])=[C:26]([CH:27]=2)[O:28][CH2:32][C:33]#[N:34])[N:9]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 57898662HCID 57898662, compound

Product 1

HCID 57898798HCID 57898798, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Cesium carbonate (12 mg) was added to a dimethylformamide solution (1 mL) of 5-(4-amino-6-benzylsulfanyl-[1,3,5]triazin-2-yl)-2,4-dichlorophenol (11 mg) obtained in Step 4 described above. A solution of α-bromoacetonitrile (3.6 mg) in dimethylformamide (0.2 mL) was added, and the resulting mixture was stirred at room temperature for 3 hours. After dilution with ethyl acetate (7 mL), the mixture was washed in succession twice with water (6 mL) and once with brine (3 mL). The mixture was then pre-dried over anhydrous sodium sulfate and filtered. The solvent was distilled off. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=8:2) to give [5-(4-amino-6-benzylsulfanyl-[1,3,5]triazin-2-yl)-2,4-dichlorophenoxy]-acetonitrile (11 mg) as white solid.

Workup

  1. washAfter dilution with ethyl acetate (7 mL), the mixture was washed in succession twice with water (6 mL) and once with brine (3 mL)
  2. dry with materialThe mixture was then pre-dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. distillationThe solvent was distilled off
  5. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-e369f4bb82144fada9f51e2a8170363f
Source dataset
uspto-grants-2012_06
Patent number
US08193351B2

Reaction notes

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