Dimethylamine, hydrochloride → HCID 57905910, compound

HRID 1670154Notes

Reaction equation

HRID 1670154 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5](O)=[O:6].Cl.[CH3:13][NH:14][CH3:15].CCN(C(C)C)C(C)C>S(Cl)(Cl)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([N:14]([CH3:15])[CH3:13])=[O:6]

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 51825203-Bromo-5-iodobenzoic acid

Product 1

HCID 57905910HCID 57905910, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 3-bromo-5-Iodo-benzoic acid (4.0 g, 12.2 mmol) in 100 mL of thionyl chloride was heated under reflux for 2 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting solid was then dissolved in 80 mL of CH2Cl2. Dimethylamine hydrochloride (1.5 g, 18.3 mmol) and DIPEA (4.3 mL, 24.5 mmol) was added and the reaction mixture was stirred at room temperature for 3 h. The resulting solution was concentrated under reduced pressure and the crude material was purified by column chromatography (Isco™ 330 g) using 50% hexanes/EtOAc as eluting solvent to afford 3.8 g (88%) of 3-bromo-5-iodo-N,N-dimethyl-benzamide as a white solid.

Workup

  1. temperatureunder reflux for 2 h
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting solid was then dissolved in 80 mL of CH2Cl2
  4. concentrationThe resulting solution was concentrated under reduced pressure
  5. customthe crude material was purified by column chromatography (Isco™ 330 g)
  6. washas eluting solvent

Sources & evidence

ORD record
ord-f3e337f674b24a7da3d40f5e4a437660
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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