Chloromethyl Methyl Ether → HCID 21515878, compound

HRID 1284188Notes

Reaction equation

HRID 1284188 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][CH3:12])=[O:10].[CH3:13][O:14][CH2:15]COC.[H-].[Na+].COCCl>CCOCC>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:13][O:14][CH3:15])[C:9]([NH:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 676515N-(2-fluorophenyl)-N'-methylurea

Product 1

HCID 21515878HCID 21515878, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 8.4 g. (0.05 mol) of N-(2-fluorophenyl)-N'-methyl urea dissolved in 200 ml. of 1,2-dimethoxyethane there was added 2.4 g. of a 50% dispersion of sodium hydride (0.05 mol) in mineral oil. The resulting mixture was stirred for 15 minutes more. Then 4.2 g. (0.05 mol) of chloromethyl methyl ether was added dropwise. After all ether was added, the mixture was stirred for 16 hours. At the end of this time it was filtered through a layer of magnesium sulfate. The filtrate was evaporated to give an oily residue which crystallized upon standing. These crystals were washed with hexane and then dried to give 6.2 g. of product, melting point 57°-59°C. Analysis: Calculated for C10H13FN2O2 : F, 8.96%; Found: F, 8.97%. The infrared spectrum showed strong adsorptions at 6.1, 6.6, 6.7, 6.9, 7.8, 9.1 and 13.5μ. The NMR spectra was consistent with the assigned structure.

Workup

  1. stirringthe mixture was stirred for 16 hours
  2. filtrationAt the end of this time it was filtered through a layer of magnesium sulfate
  3. customThe filtrate was evaporated
  4. customto give an oily residue which
  5. customcrystallized
  6. washThese crystals were washed with hexane
  7. customdried
  8. customto give 6.2 g

Sources & evidence

ORD record
ord-b2af62a44e104a499cafbf58832e98c3
Source dataset
uspto-grants-1976_08
Patent number
US03978123

Reaction notes

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