Triethylamine → Benzamide

HRID 1875276Notes

Reaction equation

HRID 1875276 reaction equation
C([N:3](CC)CC)C.[C:8]1(C)[C:9]([C:14](Cl)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=1.C(OCC)(=O)C>C(Cl)Cl>[C:14]([NH2:3])(=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 702762-Methylbenzoyl chloride

Product 1

HCID 2331BenzamideYield 337.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 391 mg (1 mmol) of 2R-hydroxy-3-[(2-methylpropyl)(4-aminophenyl)sulfonyl]amino-1S-(phenylmethyl)propylamine in 3 mL of anhydrous methylene chloride, was added 0.42 mL (3 mmol) of triethylamine, then at room temperature, 0.12 mL (0.9 mmol) of orthotoluoyl chloride was added. After 15 hours at room temp ethyl acetate was added, washed with 5% citric acid, saturated sodium bicarbonate, brine, dried, filtered and concentrated to afford 420 mg of crude material. This was chromatographed on 40 g of silica gel using 50% ethyl acetate/hexane to afford 368 mg of pure benzamide, N-[2R-hydroxy-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl) amino]-1S-(phenylmethyl)propyl]-2-methyl, m/e=516(M+Li).

Workup

  1. washwashed with 5% citric acid, saturated sodium bicarbonate, brine
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford 420 mg of crude material
  6. customThis was chromatographed on 40 g of silica gel using 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-9966db0bb5294f9b9e3bfdc5aee5efda
Source dataset
uspto-grants-2012_11
Patent number
USRE043802E1

Reaction notes

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