Sodium Bicarbonate → 5-(3-(Hydroxymethyl)phenylthio)picolinonitrile

HRID 2267052Notes

Reaction equation

HRID 2267052 reaction equation
C([O-])(O)=O.[Na+].[SH:6][C:7]1[CH:8]=[C:9]([CH2:13][OH:14])[CH:10]=[CH:11][CH:12]=1.Br[C:16]1[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[N:20][CH:21]=1>CN(C=O)C.C(OCC)(=O)C>[OH:14][CH2:13][C:9]1[CH:8]=[C:7]([S:6][C:16]2[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[N:20][CH:21]=2)[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 8171545-Bromopyridine-2-carbonitrileHCID 12813879(3-Sulfanylphenyl)methanol

Product 1

HCID 685352885-(3-(Hydroxymethyl)phenylthio)picolinonitrileYield 59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add NaHCO3 (12.0 g, 143 mmol) to a solution of (3-mercaptophenyl)methanol (10.0 g, 71.3 mmol) and 5-bromopicolinonitrile (13.0 g, 71.3 mmol) in DMF. Heat the mixture overnight. Dilute with ethyl acetate. Wash the mixture with water. Dry, filter and concentrate to afford the title compound (10.1 g, 59%) (Solidifies after standing). MS (APCI-pos) m/z (rel intensity): 243 (M+H, 100%).

Workup

  1. temperatureHeat the mixture overnight
  2. washWash the mixture with water
  3. customDry
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-ff641d7ef88a4a07965a19e3874ebf34
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

Loading…