Pyridine → 2-[(5-Nitro-2-pyridinyl)thio]ethyl 4-chlorobenzoate

HRID 731767Notes

Reaction equation

HRID 731767 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10][CH2:11][CH2:12][OH:13])=[N:8][CH:9]=1)([O-:3])=[O:2].[Cl:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.N1C=CC=CC=1>ClCCl>[Cl:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([O:13][CH2:12][CH2:11][S:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=2)=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 85014-Chlorobenzoyl chlorideHCID 433853802-[(5-Nitro-2-pyridinyl)thio]ethanol

Product 1

HCID 114938062-[(5-Nitro-2-pyridinyl)thio]ethyl 4-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A homogeneous mixture of 2-[(5-nitro-2-pyridinyl)thio]ethanol (7) (45 mg, 0.22 mmol), 4-chlorobenzoyl chloride (33 μL, 0.26 mmol) and pyridine (45 μL, 0.56 mmol) in anhydrous dichloromethane (1.5 mL) was stirred at room temperature for 48 h. The reaction mixture was quenched with 1N HCl and the organic phase was washed with saturated aqueous solution of NaHCO3, brine and then dried over anhydrous MgSO4. The crude product was purified by silica gel chromatography to give 2-[(5-nitro-2-pyridinyl)thio]ethyl 4-chlorobenzoate (8). LCMS: purity: 90%; MS (m/e): 340 (M+)

Workup

  1. customThe reaction mixture was quenched with 1N HCl
  2. washthe organic phase was washed with saturated aqueous solution of NaHCO3, brine
  3. dry with materialdried over anhydrous MgSO4
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9bbe25831e9c45c39f003ee4b950b899
Source dataset
uspto-grants-2009_09
Patent number
US07585883B2

Reaction notes

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