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

HRID 1006475Notes

Reaction equation

HRID 1006475 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 stir 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. stirringAfter stirring at room temperature overnight
  2. distillationthe solvent was distilled off
  3. washThe organic layer was washed with 50 ml of aqueous sodium hydrogen carbonate and two times with water (80 ml each)
  4. dry with materialfinally dried over sodium sulfate
  5. customRemoving the solvent in vacuo

Sources & evidence

ORD record
ord-9f706f144fc64d6ea349aed4b6b5cd35
Source dataset
uspto-grants-2004_09
Patent number
US06790852B2

Reaction notes

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