Chlorosuccinimide → 3-Chloro-6-(2,4-dichloro-phenyl)-[1,2,4]triazolo[4,3-a]pyridine-7-carbonitrile

HRID 420506Notes

Reaction equation

HRID 420506 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:18]#[N:19])=[CH:11][C:12]2[N:13]([CH:15]=[N:16][N:17]=2)[CH:14]=1.C1C(=O)N([Cl:27])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Cl:27][C:15]1[N:13]2[CH:14]=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[C:10]([C:18]#[N:19])=[CH:11][C:12]2=[N:17][N:16]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 666590346-(2,4-Dichloro-phenyl)-[1,2,4]triazolo[4,3-a]pyridine-7-carbonitrile

Product 1

HCID 666590733-Chloro-6-(2,4-dichloro-phenyl)-[1,2,4]triazolo[4,3-a]pyridine-7-carbonitrileYield 105.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 6-(2,4-dichloro-phenyl)-[1,2,4]triazolo[4,3-a]pyridine-7-carbonitrile (397 mg, 1.37 mmol, prepared according to Example 15, Step 6.4) and NCS (275 mg, 2.06 mmol) in DMF (8 mL) was heated at 50° C. and stirred for 7 h. The reaction mixture was diluted in AcOEt (50 mL) and washed with water (2×25 mL). The organic layer was dried over Na2SO41 filtered, and evaporated to give the crude title compound (466 mg, quant.). MS: 323 [M+1]+; HPLC: AtRet=2.11.

Workup

  1. washwashed with water (2×25 mL)
  2. customThe organic layer was dried over Na2SO41
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-f594acea6bac43df9ac9b2201eb23ab8
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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