Cyanogen Bromide → HCID 21916332, compound

HRID 1295849Notes

Reaction equation

HRID 1295849 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH:10][C:11]1[C:16]([NH2:17])=[CH:15][CH:14]=[CH:13][N:12]=1.C([O-])(O)=O.[Na+].Br[C:24]#[N:25]>C(O)C>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]=1[N:10]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:16]2[N:17]=[C:24]1[NH2:25]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 20780243HCID 20780243, compound

Product 1

HCID 21916332HCID 21916332, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of N2-(2,4,6-Trimethyl-phenyl)-pyridine-2,3-diamine (3.05 g, 13.4 mmol), NaHCO3 (2.03 g, 24.1 mmol) in ethanol (40 mL) at 0° C., was added a solution of BrCN (2.55 g, 24.1 mmol) in ethanol (6 mL). The resulting mixture was stirred at 0° C. For 1 h, room temperature for 8 h, and then 80° C. For 8 h. Ethanol was removed in vacuo and the residue was taken up into a separatory funnel with methylene chloride (100 mL). The mixture was washed sequentially with IN NaOH, water and brine, then the organic layer was dried over Na2SO4. After removing solvents, a brown solid was obtained. By LC-MS, the solid was a mixture of the desired product and the unreacted starting material in a ratio of 4:1 in favor of the desired product. Mass spec.: 253.17 (MH+).

Workup

  1. waitroom temperature for 8 h
  2. custom80° C
  3. waitFor 8 h
  4. customEthanol was removed in vacuo
  5. customthe residue was taken up into a separatory funnel with methylene chloride (100 mL)
  6. washThe mixture was washed sequentially with IN NaOH, water and brine
  7. dry with materialthe organic layer was dried over Na2SO4
  8. customAfter removing solvents
  9. customa brown solid was obtained

Sources & evidence

ORD record
ord-389a538b3bf248619c1437d05abb02da
Source dataset
uspto-grants-2007_07
Patent number
US07244746B2

Reaction notes

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