Hydrochloric Acid → N-(5-iodo-2-methylphenyl)benzamide

HRID 1673336Notes

Reaction equation

HRID 1673336 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.[I:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:21])=[C:18]([CH:20]=1)[NH2:19].Cl>C(N(CC)CC)C>[I:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:21])=[C:18]([NH:19][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 5228025-Iodo-o-toluidine

Product 1

HCID 57879457N-(5-iodo-2-methylphenyl)benzamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2.1 mL of benzoyl chloride was added to 70 mL of a methylene chloride solution containing 3.5 g of 5-iodo-2-methylaniline and 2.5 mL of triethylamine at room temperature and stirred at the same temperature for 30 minutes. 1.0 mol/L hydrochloric acid was added to the reaction mixture. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution, and the solvent was evaporated under reduced pressure. Diisopropyl ether and hexane were added to the obtained residue and a solid substance was separated by filtration to obtain 4.2 g of N-(5-iodo-2-methylphenyl)benzamide as pale yellow solid.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. washafter washed with a saturated sodium hydrogen carbonate aqueous solution
  4. customthe solvent was evaporated under reduced pressure
  5. additionDiisopropyl ether and hexane were added to the obtained residue
  6. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-1e7985f2dd1a4e62a094b8e4823ff079
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

Loading…