Chloromethyl Methyl Ether → 3-methoxymethoxy-N-methoxy-N-methylbenzamide

HRID 496654Notes

Reaction equation

HRID 496654 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6].[H-].[Na+].Cl[CH2:17][O:18][CH3:19]>CN(C)C=O>[CH3:17][O:18][CH2:19][O:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 218653763-hydroxy-N-methoxy-N-methylbenzamide

Product 1

HCID 223219643-methoxymethoxy-N-methoxy-N-methylbenzamideYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

69.0 g (380 mmol) of B5 were dissolved in 500 ml of dry dimethylformamide, cooled to 0° C. and 11.5 g (480 mmol) sodium hydride were added and the mixture was allowed to stirr for 10 minutes. A solution of 31.2 ml (418 mmol) (chloromethyl)methylether in 100 ml of dry diemthylformamide was added at this temperature over a period of 30 minutes. After stirring at room temperature overnight, the solvent was distilled off and the residue was partitionated between 400 ml of dichloromethane and 100 ml of water. The organic layer was washed with 50 ml of aqueous sodium hydrogen carbonate and two times with water (80 ml each) and finally dried over sodium sulfate. Removing the solvent in vacuo yielded 73.5 g (87%) B6 as a colorless oil which was used without further purification.

Workup

  1. distillationthe solvent was distilled off
  2. washThe organic layer was washed with 50 ml of aqueous sodium hydrogen carbonate and two times with water (80 ml each)
  3. dry with materialfinally dried over sodium sulfate
  4. customRemoving the solvent in vacuo

Sources & evidence

ORD record
ord-b68f639cf43b457595ecea0cf3af9f16
Source dataset
uspto-grants-2005_09
Patent number
US06946471B2

Reaction notes

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