Dimethylformamide → 4-(4-Methoxybenzylthio)-2-chloropyridine

HRID 911051Notes

Reaction equation

HRID 911051 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[CH:4][N:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][SH:20])=[CH:15][CH:14]=1.CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+]>ClCCl>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][S:20][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 804074-Methoxy-alpha-toluenethiolHCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 866347684-(4-Methoxybenzylthio)-2-chloropyridineYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flask was charged with 2-chloro-4-nitropyridine (12.75 g, 80.4 mmol), (4-methoxyphenyl)methanethiol (12.40 g, 80.4 mmol) and DMF (100 mL). Cesium carbonate (31.43 g, 96.48 mmol) was added in portions, and the mixture was stirred for 2 hours at ambient temperature. The solution was diluted with dichloromethane (250 mL) and washed with diluted sodium bicarbonate solution, dried over magnesium sulfate, filtered and evaporated. The resulting yellowish residue was triturated with hexanes and the solid was filtered to obtain the desired product (18.1 g, 85%) as a pale yellow powder.

Workup

  1. washwashed with diluted sodium bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting yellowish residue was triturated with hexanes
  6. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-66fd79e2f5ae454cabdc87966c4f083e
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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