Bromine → HCID 18509302, compound

HRID 1356676Notes

Reaction equation

HRID 1356676 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[S-:10][C:11]#[N:12].[Na+].BrBr.C(=O)(O)[O-].[Na+]>CO>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([S:10][C:11]#[N:12])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 24408BromineHCID 729132-AminobenzonitrileHCID 516871Sodium thiocyanateHCID 516892Sodium Bicarbonate

Product 1

HCID 18509302HCID 18509302, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2-aminobenzonitrile (4.00 g (33.9 mmol)) and sodium thiocyanate (3.00 g (37.0 mmol)) in methanol (20 ml), a solution of bromine (5.50 g (34.4 mmol)) in methanol (5.0 ml) was added dropwise over a period of 40 minutes under cooling with ice and with stirring. The mixture was then stirred under cooling with ice for 30 mitutes, and then neutralized with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography with chloroform as eluent to give 4.21 g (71%) of 2-amino-5-thiocyanobenzonitrile as pale yellow-white crystals.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe mixture was then stirred
  3. temperatureunder cooling with ice for 30 mitutes
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-539b44f825b748878530b55beefa7271
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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