Cyanamide → HCID 86729543, compound

HRID 631090Notes

Reaction equation

HRID 631090 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[N:14]2[N:15]=[C:16]([O:19][CH2:20][CH2:21][CH2:22][S:23][CH3:24])[CH:17]=[CH:18][C:13]2=[N:12][CH:11]=1.[N:25]#[C:26][NH2:27].[K].C([O-])(C)(C)C.BrN1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CO.O.ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[N:14]2[N:15]=[C:16]([O:19][CH2:20][CH2:21][CH2:22][S:23](=[N:27][C:26]#[N:25])[CH3:24])[CH:17]=[CH:18][C:13]2=[N:12][CH:11]=1

Participants

9

Reactant 5

HCID 9864CyanamideHCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 50987170Potassium tertbutoxideHCID 71538106HCID 71538106, compound

Product 1

HCID 86729543HCID 86729543, compoundYield 63.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

17.1 g (50.4 mmol) 3-(1-benzofuran-2-yl)-6-[3-(methylsulfanyl)propoxy]imidazo-[1,2-b]pyridazine and 2.65 g (63.0 mmol) cyanamide were dissolved in 86 mL methanol. At 20-25° C. 7.35 g (65.5 mmol) potassium-tert.-butanolate were added in portions. 11.7 g (65.5 mmol) N-bromosuccinimide were added in portions and it was stirred one hour at room temperature. 250 mL dichloromethane were added and stirred a couple of minutes. 64 mL 10% sodium thiosulfate solution and 22 mL water were added. The layers were separated and the aqueous phase was extracted twice with 30 mL of dichloromethane. The combined organic phases were washed twice with 20 mL water, dried over magnesium sulfate, and concentrated. The residue was crystallized from dichloromethane and tert-butyl methyl ether to yield 12.08 g (63%) of a yellow powder.

Workup

  1. customAt 20-25° C
  2. stirringstirred a couple of minutes
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted twice with 30 mL of dichloromethane
  5. washThe combined organic phases were washed twice with 20 mL water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was crystallized from dichloromethane and tert-butyl methyl ether

Sources & evidence

ORD record
ord-3e01cefc50db44d59a0267e056d4c231
Source dataset
uspto-grants-2016_04
Patent number
US09320737B2

Reaction notes

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