2-Bromoethanol → 2-[(5-Nitro-2-pyridinyl)thio]ethanol

HRID 731766Notes

Reaction equation

HRID 731766 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.Br[CH2:12][CH2:13][OH:14].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([S:1][CH2:12][CH2:13][OH:14])=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 178526723C5H4N2O2S

Product 1

HCID 433853802-[(5-Nitro-2-pyridinyl)thio]ethanolYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

A heterogeneous mixture of 2-mercapto-5-nitropyridine (4) (0.50 g, 3.2 mmol), 2-bromoethanol (1) (0.238 mL, 3.3 mmol), and K2CO3 (2.0 g, 14 mmol) in acetone (11 mL) was stirred at 55° C. for 1 h. The cooled reaction mixture was filtered through Celite®, concentrated, and then purified by silica gel chromatography to give 2-[(5-nitro-2-pyridinyl)thio]ethanol (7) as an orange solid (0.545 g, 2.72 mmol). 1H NMR (CDCl3): δ 9.20 (d, J=3.0 Hz, 1H), 8.23 (dd, J=3.0 and 8.7 Hz, 1H), 7.36 (d, J=8.7 Hz, 1H), 3.94 (t, J=6.0 Hz, 2H), 3.46 (d, J=6.0 Hz, 2H); LCMS: purity: 96%; MS (m/e): 201(MH+).

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas filtered through Celite®
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-448260ea704246db964b2ffd99f97730
Source dataset
uspto-grants-2009_09
Patent number
US07585883B2

Reaction notes

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