Bromine → (2-Amino-1,3-benzothiazol-6-yl)acetonitrile

HRID 1452957Notes

Reaction equation

HRID 1452957 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[S-:11][C:12]#[N:13].[K+].BrBr>CC(O)=O>[NH2:13][C:12]1[S:11][C:3]2[CH:4]=[C:5]([CH2:8][C:9]#[N:10])[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 770004-AminophenylacetonitrileHCID 516872Potassium thiocyanate

Product 1

HCID 21298164(2-Amino-1,3-benzothiazol-6-yl)acetonitrileYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 2-(4-aminophenyl)acetonitrile (6.00 g, 45.4 mmol) in AcOH (70 mL) was added potassium thiocyanate (17.6 g, 181 mmol) at rt in one portion. The mixture was stirred at rt until it became a clear solution. To this solution was then added a solution of bromine (2.3 mL, 44.9 mmol) in AcOH (30 mL) at rt over 1 hr. The resulting mixture was stirred at rt for 4 hr. The precipitate that formed during the reaction was collected by suction filtration, and then suspended into water (100 mL). The pH value of the aqueous suspension was adjusted to 8 with concentrated ammonium hydroxide. The insoluble product (7.39 g, 86% yield) was collected as a pale yellow solid by suction filtration and dried over Drierite® under vacuum at 65° C.

Workup

  1. stirringThe resulting mixture was stirred at rt for 4 hr
  2. customThe precipitate that formed during the reaction
  3. filtrationwas collected by suction filtration

Sources & evidence

ORD record
ord-e9ab6b6df075408894023be2413858d7
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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