Dimethylformamide → 4'-Nitro-3'-(2-pyridylthio)acetophenone

HRID 1087184Notes

Reaction equation

HRID 1087184 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.CC(C)([O-])C.[K+].CN(C)C=O.[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[CH:24][C:23]=1Cl)([O-:21])=[O:20]>C1(C)C=CC=CC=1.O>[N+:19]([C:22]1[CH:23]=[CH:24][C:25]([C:28](=[O:30])[CH3:29])=[CH:26][C:27]=1[S:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)([O-:21])=[O:20]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 104427551-(3-Chloro-4-nitrophenyl)ethanoneHCID 23665647Potassium tert-butoxideHCID 178418616HCID 178418616, compound

Product 1

HCID 100847124'-Nitro-3'-(2-pyridylthio)acetophenoneYield 53.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2-mercaptopyridine (1.7 g), potassium t-butoxide (1.7 g) and N,N-dimethylformamide (3 ml) in toluene (15 ml) was stirred at room temperature for 30 minutes. To the mixture was added 4'-nitro-3'-chloroacetophenone (1.5 g) and the resulting mixture was stirred overnight. Water was added and the insoluble material was filtered, washed with toluene and dried to give crystals of 4'-nitro-3'-(2-pyridylthio)acetophenone (1.1 g).

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. filtrationthe insoluble material was filtered
  3. washwashed with toluene
  4. customdried

Sources & evidence

ORD record
ord-47589cb8713c42af987a7ae953e2e37f
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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