Dimethyl Sulfoxide → HCID 12906163, compound

HRID 1833826Notes

Reaction equation

HRID 1833826 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[C:10]([OH:11])=[CH:9][CH:8]=[C:7]([Cl:12])[N:6]=1.CS(C)=O.[CH2:17]([N:19]([CH2:24][CH3:25])[C:20](=[O:23])[CH2:21]Cl)[CH3:18]>CO>[CH2:17]([N:19]([CH2:24][CH3:25])[C:20](=[O:23])[CH2:21][O:11][C:10]1[C:5]([Cl:4])=[N:6][C:7]([Cl:12])=[CH:8][CH:9]=1)[CH3:18]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 16844Chloro-N,N-diethylacetamideHCID 1043172,6-Dichloropyridin-3-olHCID 10942334Sodium Methoxide

Product 1

HCID 12906163HCID 12906163, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4.6 g of sodium methylate (0.2 mole) in 50 ml of absolute methanol is slowly added at room temperature to 33.4 g (0.2 mole) of 2,6-dichloropyridin-3-ol. There is then added, with gentle heating, 100 to 150 ml of dimethylsulphoxide until the cloudy solution becomes clear. The solution is then heated to 80°-90° and methanol is distilled off. The reaction solution is cooled and an addition is slowly made dropwise at 0°-10° C of a solution of 60 g (0.2 mole) of chloroacetic acid diethylamide (dissolved in 300 ml of dimethylsulphoxide). After the dropwise addition is completed, the reaction mixture is stirred at room temperature for a further hour. The solvent is distilled off under reduced pressure; the oil remaining is taken up in ether, washed with water, dried and freed from solvent to leave N,N-diethyl-(2,6-dichloro-3-pyridyl)-oxy-acetic acid amide, which boils at 137°/0.4 torr; yield: 35 g (62% of theory). Treatment with ethereal hydrochloric acid yields the hydrochloride, which is recrystallised from isopropanol.

Workup

  1. temperatureThe solution is then heated to 80°-90°
  2. distillationmethanol is distilled off
  3. temperatureThe reaction solution is cooled
  4. additionan addition
  5. additionAfter the dropwise addition
  6. distillationThe solvent is distilled off under reduced pressure
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-b003ba466fee45e9afc63e67b7fa2c16
Source dataset
uspto-grants-1978_01
Patent number
US04067725

Reaction notes

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