Methylamine → 2-Iodo-N-methylbenzamide

HRID 493094Notes

Reaction equation

HRID 493094 reaction equation
S(Cl)(Cl)=O.[I:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](O)=[O:9].[CH3:15][NH2:16]>C1(C)C=CC=CC=1>[I:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH:16][CH3:15])=[O:9]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 69412-Iodobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 6158522-Iodo-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (29.4 mL, 404 mmol) is added to a solution of (2-iodo-benzoic acid (50.0 g, 202 mmol) in dry toluene (600 mL). The mixture is heated to reflux for 4 hours and the solvent is removed in vacuo. The remanence is redissolved in dry toluene (600 mL) and cooled to 0° C. 40% methylamine (aq., 94.1 mL, 1.21 mol) is added dropwise at 0-5° C. during 30 minutes. The mixture is then stirred at ambient temperature for 16 hours, poured onto water (300 mL) and extracted with ethyl acetate (3×300 mL) The combined organic fractions are washed successively with saturated sodium bicarbonate solution (250 mL) and brine (250 mL), dried (MgSO4) and concentrated in vacuo. This gives 50.8 g (96%) of crystalline 2-iodo-N-methyl-benzamide.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 4 hours
  3. customthe solvent is removed in vacuo
  4. dissolutionThe remanence is redissolved in dry toluene (600 mL)
  5. additionpoured onto water (300 mL)
  6. extractionextracted with ethyl acetate (3×300 mL) The combined organic fractions
  7. washare washed successively with saturated sodium bicarbonate solution (250 mL) and brine (250 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e58a132ef77a4c108aeb4fe3605f7c68
Source dataset
uspto-grants-2009_05
Patent number
US07534791B2

Reaction notes

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