Cyanogen Bromide → HCID 178482987, compound

HRID 1159185Notes

Reaction equation

HRID 1159185 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]([CH3:14])[CH2:9][CH:10]([NH2:13])[CH2:11][NH2:12])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[N:21]#[C:22]Br>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]([CH2:9][CH:10]2[CH2:11][NH:12][C:22]([NH2:21])=[N:13]2)[CH3:14])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 68644158HCID 68644158, compound

Product 1

HCID 178482987HCID 178482987, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N1-(3-Chloro-phenyl)-N1-methyl-propane-1,2,3-triamine (0.321 g, 1.5 mmol) was dissolved in tetrahydrofurane (5 ml) and potassium carbonate (0.249 g, 1.8 mmol) was added. Under cooling with an ice-bath a solution of cyanogen bromide (0.191 g, 1.8 mmol) in tetrahydrofurane (5 ml) was added dropwise. The cooling bath was removed and stirring was continued for one hour. Ethyl acetate (50 ml) and water (20 ml) were added and the organic layer was separated. The mixture was extracted again with ethyl acetate. The combined organic layers were dried over magnesium sulfate and evaporated. The residue was recrystallised from ethyl acetate to yield 0.1 g (28%) of a white solid; MS (ISP): 239.2 ((M+H)+).

Workup

  1. additionwas added dropwise
  2. customThe cooling bath was removed
  3. additionEthyl acetate (50 ml) and water (20 ml) were added
  4. customthe organic layer was separated
  5. extractionThe mixture was extracted again with ethyl acetate
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. customevaporated
  8. customThe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-68896c109084470bb7632addfe745cd0
Source dataset
uspto-grants-2010_10
Patent number
US07812047B2

Reaction notes

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