Ethyl Acetate → HCID 68276433, compound

HRID 1487375Notes

Reaction equation

HRID 1487375 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:15]=[C:16]([SH:21])[CH:17]=[C:18]([Cl:20])[CH:19]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C(#N)C>[Cl:13][C:14]1[CH:15]=[C:16]([S:21][C:2]2[N:7]=[C:6]([C:8]#[N:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=2)[CH:17]=[C:18]([Cl:20])[CH:19]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27360963,5-DichlorobenzenethiolHCID 133817056-Chloro-3-nitropyridine-2-carbonitrile

Product 1

HCID 68276433HCID 68276433, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-chloro-3-nitropicolinonitrile (3.70 g, 0.02 mol), 3,5-dichlorobenzenethiol (3.60 g, 0.02 mol) and K2CO3 (5.6 g, 0.04 mol) in 100 ml of acetonitrile is carried at 70° C. for 16 hours. The crude reaction product is diluted in an ethyl acetate fraction and washed using an aqueous phase. The organic phase is dried with sodium sulfate and the residue is purified by silica gel chromatography (AcOEt/petroleum ether) to yield 5.4 g (80%) of a yellow solid.

Workup

  1. customThe crude reaction product
  2. washwashed
  3. dry with materialThe organic phase is dried with sodium sulfate
  4. customthe residue is purified by silica gel chromatography (AcOEt/petroleum ether)

Sources & evidence

ORD record
ord-2e573e30ff634d6996d1424fc4f6d6c7
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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