Triethylamine → Benzamide

HRID 1934473Notes

Reaction equation

HRID 1934473 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-d54f9b16a2e348c5ab1bfeeb8acc64d7
Source dataset
uspto-grants-2002_05
Patent number
US06384036B1

Reaction notes

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