Thionyl Chloride → 4-bromo-N-cyclopropyl-2-methylbenzamide

HRID 2185373Notes

Reaction equation

HRID 2185373 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH3:11])[CH:3]=1.O=S(Cl)Cl.[CH:16]1([NH2:19])[CH2:18][CH2:17]1>CCOC(C)=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:19][CH:16]2[CH2:18][CH2:17]2)=[O:8])=[C:4]([CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 69828CyclopropylamineHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 225688404-bromo-N-cyclopropyl-2-methylbenzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-bromo-2-methylbenzoic acid and SOCl2 was refluxed for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in 30 mL CH2Cl2 and combined with cyclopropyl amine (810.0 mg, 14.3 mmols) and pyridine,(2.05 g, 26.0 mmols). The solution was stirred for 18 hours and then diluted with EtOAc before being washed with 5% aqueous HCl, saturated NaHCO3, and saturated aqueous NaCl. The solution was dried (MgSO4) and concentrated under reduced pressure leaving the title compound as a colorless solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 30 mL CH2Cl2
  3. washbefore being washed with 5% aqueous HCl, saturated NaHCO3, and saturated aqueous NaCl
  4. dry with materialThe solution was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-41fb3b79d4414fe086cf8131c1886934
Source dataset
uspto-grants-2002_06
Patent number
US06399774B1

Reaction notes

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