Sodium Iodide → N-(5-Hydroxymethyl-2-methylphenyl)-N-(3-methoxypropyl)acetamide

HRID 1176221Notes

Reaction equation

HRID 1176221 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:13])=[C:7]([NH:9][C:10](=[O:12])[CH3:11])[CH:8]=1.[H-].[Na+].Cl[CH2:17][CH2:18][CH2:19][O:20][CH3:21].[I-].[Na+]>CN(C)C=O>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:13])=[C:7]([N:9]([CH2:17][CH2:18][CH2:19][O:20][CH3:21])[C:10](=[O:12])[CH3:11])[CH:8]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 1189271-Chloro-3-methoxypropaneHCID 14543056N-[5-(Hydroxymethyl)-2-methylphenyl]acetamide

Product 1

HCID 68506164N-(5-Hydroxymethyl-2-methylphenyl)-N-(3-methoxypropyl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The solution of 0.892 g of N-(5-hydroxymethyl-2-methylphenyl)acetamide in 8 ml of N,N-dimethylformamide is cooled to 0° C. with stirring and admixed with 0.16 g of sodium hydride dispersion (60%). The mixture is stirred at 0° C. over 30 minutes and subsequently admixed with 0.489 ml of 1-chloro-3-methoxypropane and 60 mg of sodium iodide. The reaction mixture is stirred at 80° C. over 48 hours and poured onto water (50 ml). The mixture is extracted with ethyl acetate (2×50 ml). The organic phases are washed successively with water (2×50 ml) and brine (1×50 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as an orange oil from the residue by means of flash chromatography (SiO2 60F). Rt=2.73.

Workup

  1. stirringThe mixture is stirred at 0° C. over 30 minutes
  2. stirringThe reaction mixture is stirred at 80° C. over 48 hours
  3. additionpoured onto water (50 ml)
  4. extractionThe mixture is extracted with ethyl acetate (2×50 ml)
  5. washThe organic phases are washed successively with water (2×50 ml) and brine (1×50 ml)
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-fe0ca86622fe4311b71bc941b8924936
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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