Ethyl Acetate → HCID 68276433, compound

HRID 334404Notes

Reaction equation

HRID 334404 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-4123714264154bc0a8be3adae746fff8
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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