Triethylamine → Benzamide

HRID 553361Notes

Reaction equation

HRID 553361 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-ff2021606e9a467586392bd68832c7ae
Source dataset
uspto-grants-2011_11
Patent number
USRE042889E1

Reaction notes

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