2-Mercaptoethanol → 2-(6-Methyl-5-nitro-pyridin-2-ylsulfanyl)-ethanol

HRID 1811571Notes

Reaction equation

HRID 1811571 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.[SH:12][CH2:13][CH2:14][OH:15].[OH-].[K+]>>[CH3:8][C:6]1[N:7]=[C:2]([S:12][CH2:13][CH2:14][OH:15])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 3

HCID 15672-MercaptoethanolHCID 14797Potassium HydroxideHCID 2531236-Chloro-2-methyl-3-nitropyridine

Product 1

HCID 114244292-(6-Methyl-5-nitro-pyridin-2-ylsulfanyl)-ethanol

Procedure

To an ice-cooled solution of 6-chloro-2-methyl-3-nitropyridine (2.17 g, 13 mmol) in 2-mercaptoethanol (5 mL, 71 mmol), potassium hydroxide (1.52 g, 27 mmol) was added. Mixture was stirred at room temperature for 2 h and then extracted with NaOH solution and CH2Cl2. Organic phases were dried over MgSO4, filtered, and concentrated to give 2-(6-methyl-5-nitro-pyridin-2-ylsulfanyl)-ethanol as a brown oil (60% pure, 3.25 g, 72%). 1HNMR (CDCl3, 400 MHz) δ 2.87-2.90 (m, 6H), 3.43-3.46 (t, J=5.6 Hz, 2H), 7.22-7.24 (d, J=8.7 Hz, 1H), 8.15-8.17 (d, J=8.7 Hz, 1H). Exact mass calculated for C8H10N2O3S 214.04 found 215.1 (MH+).

Workup

  1. additionwas added
  2. extractionextracted with NaOH solution and CH2Cl2
  3. dry with materialOrganic phases were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b14a028bcb14667a47111836e646bd6
Source dataset
uspto-grants-2013_01
Patent number
US08362248B2

Reaction notes

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