Methylamine → N-Methyl-2-Methoxy-3,6-Dichlorobenzamide

HRID 485195

Reaction equation

HRID 485195 reaction equation
[CH3:1][O:2][C:3]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]([Cl:13])[C:4]=1[C:5](Cl)=[O:6].[CH3:14][NH2:15]>CCOCC>[CH3:14][NH:15][C:5](=[O:6])[C:4]1[C:8]([Cl:13])=[CH:9][CH:10]=[C:11]([Cl:12])[C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 6329Methylamine2×HCID 82609Benzoyl chloride, 3,6-dichloro-2-methoxy-

Product 1

HCID 14156699N-Methyl-2-Methoxy-3,6-Dichlorobenzamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
4 °C

Procedure

Methylamine (146.1 grams; 4.70 moles) contained in 40% aqueous methyl amine solution (365.4 grams) was placed in a 3-liter, 3-necked glass reaction flask equipped with addition funnel, stirrer, thermometer and reflux condenser and containing ether (1200 ml) cooled to 4° C. 2-methoxy-3,6-dichlorobenzoic acid chloride (375 grams; 1.56 moles) in ether (50 ml) was added dropwise with stirring maintaining the temperature below 8° C. After the completion of the addition the reaction mixture was stirred for an additional two hours at a temperature of between 2° and 5° C. The insoluble white solid was filtered with suction, washed with water, transferred to a 3-liter beaker and stirred fifteen (15) minutes with 10% sodium carbonate (2 liters). The insoluble white solid was filtered with suction, washed with water and dried. The product weighed 352 grams and had a melting point of 172.5°-175° C.

Workup

  1. customwas placed in a 3-liter, 3-necked glass reaction flask
  2. customequipped with addition funnel, stirrer
  3. temperaturethermometer and reflux condenser
  4. temperaturemaintaining the temperature below 8° C
  5. additionAfter the completion of the addition the reaction mixture
  6. stirringwas stirred for an additional two hours at a temperature of between 2° and 5° C
  7. filtrationThe insoluble white solid was filtered with suction
  8. washwashed with water
  9. stirringstirred fifteen (15) minutes with 10% sodium carbonate (2 liters)
  10. filtrationThe insoluble white solid was filtered with suction
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-19573ff6a9384c6aa70d895de30085d0
Source dataset
uspto-grants-1985_08
Patent number
US04536210

Linked notes

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