1,2-Dichloroethane → HCID 15766267, compound

HRID 439550Notes

Reaction equation

HRID 439550 reaction equation
ClCCCl.[Br:5][C:6]1[C:14]([Cl:15])=[C:13]([Cl:16])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O.S(Cl)(Cl)=O.[CH3:21][NH:22][CH2:23][CH3:24]>O1CCCC1.CN(C)C=O>[CH2:23]([N:22]([CH3:21])[C:8](=[O:10])[C:7]1[CH:11]=[CH:12][C:13]([Cl:16])=[C:14]([Cl:15])[C:6]=1[Br:5])[CH3:24]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 12219N-MethylethylamineHCID 24386Thionyl ChlorideHCID 22411757HCID 22411757, compound

Product 1

HCID 15766267HCID 15766267, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

200 ml of 1,2-dichloroethane, 14 g (0.052 mol) of 2-bromo-3,4-dichlorobenzoic acid and 2 ml of N,N-dimethylformamide are introduced successively into a 500 ml round-bottomed flask. 11.5 ml of thionyl chloride (0.078 mol) are then run in dropwise with stirring and while cooling at 0° C. When the addition is finished, the reaction mixture is heated progressively to 55° C. over 2 hours and then evaporated to dryness. The residue is taken up in 50 ml of tetrahydrofuran and then poured dropwise into a solution containing 13 ml (0.15 mol) of N-methylethylamine in 50 ml of tetrahydrofuran maintained at a temperature below 10° C. When the addition is finished, the reaction mixture is stirred at room temperature for one hour and then evaporated to dryness. The residue is taken up in dichloromethane and washed successively with 1N HCl and distilled water. After drying over magnesium sulfate, the organic phase is evaporated under reduced pressure to provide 12.4 g (yield: 80%) of N-ethyl-N-methyl-2-bromo-3,4-dichlorobenzamide in the form of a white solid melting at 71° C.

Workup

  1. additionWhen the addition
  2. temperaturethe reaction mixture is heated progressively to 55° C. over 2 hours
  3. customevaporated to dryness
  4. additionpoured dropwise into a solution
  5. temperaturemaintained at a temperature below 10° C
  6. additionWhen the addition
  7. stirringthe reaction mixture is stirred at room temperature for one hour
  8. customevaporated to dryness
  9. washwashed successively with 1N HCl
  10. distillationdistilled water
  11. dry with materialAfter drying over magnesium sulfate
  12. customthe organic phase is evaporated under reduced pressure

Sources & evidence

ORD record
ord-c149164c6da0478c9b4846b773d4f185
Source dataset
uspto-grants-1996_05
Patent number
US05514719

Reaction notes

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