Water → HCID 22460786, compound

HRID 1637616Notes

Reaction equation

HRID 1637616 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[C:12]([CH3:13])=[C:11]([O:14][CH2:15][CH2:16]CO)[CH:10]=[CH:9][N:8]=1.O.C(=O)(O)[O-].[Na+].Cl[CH2:26][Cl:27]>>[Cl:3][CH2:6][C:7]1[C:12]([CH3:13])=[C:11]([O:14][CH2:15][CH2:16][CH2:26][Cl:27])[CH:10]=[CH:9][N:8]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6344Dichloromethane2×HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 187994083-((2-(Hydroxymethyl)-3-methylpyridin-4-yl)oxy)propan-1-ol

Product 1

HCID 22460786HCID 22460786, compound

Procedure

A solution of 2.3 ml (31.7 mmol) of thionyl chloride in 5 ml of dichloromethane is added dropwise at 0° C. to a solution of 2.5 g (12.6 mmol) of 3-(2-hydroxymethyl-3-methylpyridin-4-yloxy)propan-1-ol in 20 ml of dichloromethane and the mixture is subsequently stirred at room temperature for a further 16 h. Water (20 ml) is then added, and the mixture is adjusted to pH 8 using sodium bicarbonate solution and extracted with 3×20 ml of dichloromethane. The organic extracts are washed with water, dried over magnesium sulfate and concentrated. The residual oil (2.8 g) is employed in stage b) without further purification.

Workup

  1. extractionextracted with 3×20 ml of dichloromethane
  2. washThe organic extracts are washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customwithout further purification

Sources & evidence

ORD record
ord-576ecf4a0d86447786094a8daaec0d13
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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