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

HRID 9167

Reaction equation

HRID 9167 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[CH:4][CH:3]=1.[S-:10][C:11]#[N:12].[K+].BrBr.[C:16](#[N:23])C1C=CC=CC=1>C(O)(=O)C.O>[NH2:12][C:11]1[S:10][C:3]2[CH:4]=[C:5]([CH2:6][C:16]#[N:23])[CH:8]=[CH:9][C:2]=2[N:1]=1

Participants

7

Reactant 4

HCID 7505BenzonitrileHCID 133964-AminobenzonitrileHCID 24408BromineHCID 516872Potassium thiocyanate

Product 1

HCID 21298164(2-Amino-1,3-benzothiazol-6-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
16 °C

Procedure

2 grams of 4-aminobenzonitrile is dissolved in about 40 mL acetic acid and the solution is cooled to about 16° C. About 3.3 g of potassium thiocyanate is added and the flask is equipped with an addition funnel. The addition funnel is charged with about 2.7 g bromine and about 5 ml acetic acid. This dark solution is then added to the benzonitrile solution in a dropwise fashion under good agitation and allowed to stir for about 16 hours. The slurry is then drowned into water and filtered. The presscake is washed well with water, reslurried in dilute aqueous alkali and filtered. Again the presscake is washed well with water. After drying in vacuo, about 2 grams is isolated.

Workup

  1. customthe flask is equipped with an addition funnel
  2. filtrationfiltered
  3. washThe presscake is washed well with water
  4. filtrationfiltered
  5. washAgain the presscake is washed well with water
  6. customAfter drying in vacuo
  7. customabout 2 grams is isolated

Sources & evidence

ORD record
ord-d0a3bdf85e9b4840981acc50d0208080
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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