Hydrochloric Acid → HCID 57879359, compound

HRID 1673348Notes

Reaction equation

HRID 1673348 reaction equation
CN(C)C=O.Cl.[CH3:7][C:8]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][C:9]=1[NH2:10].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>C(OCC)(=O)C.C(N(CC)CC)C>[CH3:7][C:8]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:11][C:9]=1[NH:10][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 7412Benzoyl chlorideHCID 67344504HCID 67344504, compound

Product 1

HCID 57879359HCID 57879359, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5 mL of N,N-dimethylformamide containing 0.50 g of 2-methyl-5-phenoxyaniline hydrochloride, 0.91 mL of triethylamine and 0.27 mL of benzoyl chloride were added sequentially while ice-cooled sequentially and stirred at room temperature for 3 hours. Ethyl acetate and 1.0 mol/L hydrochloric acid were added to the reaction mixture. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 1.0 mol/L hydrochloric acid, a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue and a solid substance was separated by filtration to obtain 0.42 g of N-(2-methyl-5-phenoxyphenyl)benzamide as white solid.

Workup

  1. temperaturecooled sequentially
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. washafter washed with 1.0 mol/L hydrochloric acid
  5. customa saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  6. additionHexane and diisopropyl ether were added to the obtained residue
  7. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-5b39d657695b4eb2a06fc56a898b3c06
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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