Ethanol → 5-Cyanomethylbenz-2,1,3-thiadiazole

HRID 456593

Reaction equation

HRID 456593 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH:11]=1)=[N:8][S:9][N:10]=2.C(O)C.[C-:15]#[N:16].[K+]>O>[N:10]1[S:9][N:8]=[C:7]2[CH:11]=[C:3]([CH2:2][C:15]#[N:16])[CH:4]=[CH:5][C:6]=12

Participants

5

Reactant 3

HCID 702EthanolHCID 9032Potassium CyanideHCID 5910045-(Bromomethyl)-2,1,3-benzothiadiazole

Product 1

HCID 695224455-Cyanomethylbenz-2,1,3-thiadiazoleYield 53.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-bromomethyl-benzo[1,2,5]thiadiazole [RN65858-50-6](7.0 g, 30 mmol), ethanol (50 ml)and a solution of potassium cyanide (2.3 g, 36 mmol) in water (25 ml) was stirred at 50° C. for 15 hours. The alcoholic solution was concentrated and the residue suspended in water. The solid was collected by filtration, washed with water and dried in vacuo to give benzo[1,2,5]thiadiazol-5-yl-acetonitrile (2.8 g, 47%)

Workup

  1. concentrationThe alcoholic solution was concentrated
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-a391e509cf0c4b54be8190b45336aff2
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Linked notes

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