1,2-Dimethoxyethane → HCID 21515857, compound

HRID 1284186Notes

Reaction equation

HRID 1284186 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].COCCOC.[H-].[Na+].[CH3:21][S:22][CH2:23]Cl>O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:21][S:22][CH3:23])[C:9]([NH:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 80711,2-Dimethoxyethane2×HCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 676515N-(2-fluorophenyl)-N'-methylurea

Product 1

HCID 21515857HCID 21515857, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 16.8 g. (0.1 mol) of N-(2-fluorophenyl)-N'-methyl urea in 250 ml. of 1,2-dimethoxyethane was cooled to 0°C. Then 4.8 g. (0.1 mol) of a 50% dispersion of sodium hydride in mineral oil was added slowly. After addition was complete, the solution was stirred for 15 minutes. This solution was added slowly to a stirred solution of 9.7 g. (0.1 mol) of chloromethyl methyl sulfide in 100 ml. of 1,2-dimethoxyethane. The resulting mixture was stirred at room temperature for 65 hours. At the end of this time, the precipitate was removed by filtration and the resulting filtrate was evaporated to give an oil which solidified upon adding water. The solid was isolated by filtration, washed with hexane and dried. Recrystallization from a hexene-benzene mixture gave 12 g. crystalline solid, melting point 102.5°-103°C. An infrared spectrum showed sharp, strong adsorptions at 3.0, 6.1, 13.05 and 13.2μ .

Workup

  1. additionAfter addition
  2. additionThis solution was added slowly to a stirred solution of 9.7 g
  3. stirringThe resulting mixture was stirred at room temperature for 65 hours
  4. customAt the end of this time, the precipitate was removed by filtration
  5. customthe resulting filtrate was evaporated
  6. customto give an oil which
  7. customThe solid was isolated by filtration
  8. washwashed with hexane
  9. customdried
  10. customRecrystallization from a hexene-benzene mixture
  11. customgave 12 g

Sources & evidence

ORD record
ord-2bee7b5812cc4a81bbc0e56632efe4b5
Source dataset
uspto-grants-1976_08
Patent number
US03978123

Reaction notes

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