Cyanogen Bromide → HCID 178429220, compound

HRID 568818Notes

Reaction equation

HRID 568818 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][C:6](=[O:12])[C:5]2([CH3:14])[CH3:13].[N:15]#[C:16]Br>C(O)C>[CH3:13][C:5]1([CH3:14])[C:4]2[C:8](=[CH:9][C:10]3[NH:11][C:16]([NH2:15])=[N:1][C:2]=3[CH:3]=2)[NH:7][C:6]1=[O:12]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 135892372H-Indol-2-one, 5,6-diamino-1,3-dihydro-3,3-dimethyl-

Product 1

HCID 178429220HCID 178429220, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.00 g. (0.016 mole) 5,6-diamino-3,3-dimethylindolin-2-one are suspended in 100 ml. ethanol and mixed at ambient temperature with 1.82 g. (0.017 mole) cyanogen bromide and stirred for 2 hours. The solvent is removed in a vacuum and the residue is dissolved in ethanol, treated with active charcoal and the product precipitated out by the addition of acetone. The product is crystallised from acetone and a little ethanol to give 1.05 g. (22% of theory) of the title compound in the form of the hydrobromide; m.p. 300°-305° C.

Workup

  1. customThe solvent is removed in a vacuum
  2. dissolutionthe residue is dissolved in ethanol
  3. additiontreated with active charcoal
  4. customthe product precipitated out by the addition of acetone
  5. customThe product is crystallised from acetone
  6. customa little ethanol to give 1.05 g

Sources & evidence

ORD record
ord-083791cb6af04aafa82eac936ee269af
Source dataset
uspto-grants-1988_03
Patent number
US04730003

Reaction notes

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