Methane → HCID 19867132, compound

HRID 1199546Notes

Reaction equation

HRID 1199546 reaction equation
[CH3:1][O-:2].[Na+].Br[C:5]1[CH:6]=[C:7]([CH:10]=[C:11](Br)[C:12]=1[NH:13][CH3:14])[C:8]#[N:9].CN(C)[CH:18]=[O:19].C>CO.[Cu]Cl.O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:19][CH3:18])[C:12]=1[NH:13][CH3:14])[C:8]#[N:9]

Participants

9

Reactant 4

HCID 297MethaneHCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 19867130HCID 19867130, compound

Product 1

HCID 19867132HCID 19867132, compound

Reagents, catalysts & solvents 4

HCID 62652Cuprous chlorideCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

167 g of sodium methoxide are dissolved in 460 ml of methanol while stirring and cooling. Thereafter, 25 g of copper(I) chloride and 153 g of 3,5-dibromo-4-methylaminobenzonitrile as well as 76 ml of dimethylformamide are added. The mixture is heated to reflux for 4.5 hours, cooled to 25°-30° C. and treated with 450 ml of toluene, 450 ml of water and 7.5 g of active charcoal. The mixture is filtered and the organic phase is washed with a solution of 160 ml of water and 16 ml of acetic acid (pH about 6). The organic phase is separated and concentrated under reduced pressure, whereby there are obtained about 91 g of 3,5-dimethoxy-4-methylaminobenzonitrile in the form of an oily residue which crystallizes upon standing and which is used in this form in the next reaction step.

Workup

  1. temperaturecooling
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 4.5 hours
  4. temperaturecooled to 25°-30° C.
  5. filtrationThe mixture is filtered
  6. washthe organic phase is washed with a solution of 160 ml of water and 16 ml of acetic acid (pH about 6)
  7. customThe organic phase is separated
  8. concentrationconcentrated under reduced pressure, whereby there

Sources & evidence

ORD record
ord-d6e9209de0a6431fa5b8a49cd29f3a14
Source dataset
uspto-grants-1990_02
Patent number
US04900859

Reaction notes

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