Potassium Cyanide → HCID 22144526, compound

HRID 1824797Notes

Reaction equation

HRID 1824797 reaction equation
Br[CH2:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[S:11][C:7]=2[CH:6]=[C:5]([O:20][CH3:21])[CH:4]=1.[C-:22]#[N:23].[K+]>C(O)C.O>[C:22]([CH2:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[S:11][C:7]=2[CH:6]=[C:5]([O:20][CH3:21])[CH:4]=1)#[N:23]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 22144497HCID 22144497, compound

Product 1

HCID 22144526HCID 22144526, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-bromomethyl-6-methoxy-2-(4-methoxy-phenyl)-benzothiazole (0.47 g, 1.29 mmol) in ethanol (6 mL) was added a solution of potassium cyanide (0.1 g, 1.54 mmol) in water (0.5 mL). The mixture was refluxed for 1.5 h, then cooled to room temperature. Ethanol was evaporated and the mixture was extracted with ethylacetate. After chromatographic purification gave 4-cyanomethyl-6-methoxy-2-(4-methoxy-phenyl)-benzothiazole as a yellow solid (0.29 g, 73% yield). Mass spec: MH+=311.

Workup

  1. temperatureThe mixture was refluxed for 1.5 h
  2. customEthanol was evaporated
  3. extractionthe mixture was extracted with ethylacetate
  4. customAfter chromatographic purification

Sources & evidence

ORD record
ord-124df5bcdf9c4ce19aef9352982906d3
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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