Hydrochloric Acid → Valeranilide

HRID 276242Notes

Reaction equation

HRID 276242 reaction equation
C([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])CC.CCN([CH2:16][CH3:17])CC.C(O[C:22](=[O:24])[CH3:23])(=O)C.Cl.[CH2:26](Cl)Cl>>[CH2:26]([CH2:23][C:22]([NH:6][C:5]1[CH:4]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:24])[CH2:16][CH3:17]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 157592-Propylaniline

Product 1

HCID 82501ValeranilideYield 67%

Procedure

To a solution of 2-n-propylaniline (8.91 g, 66 mmol) and Et3N (14 mL, 106 mmol) in CH2Cl2 (60 mL) was added acetic anhydride (10.9 mL, 99 mmol) dropwise. The resulting mixture was allowed to stir at room temp. overnight, then was treated with a 1N HCl solution (40 mL). The acidic mixture was extracted with CH2Cl2 (2×30 mL). The combined organic layers were sequentially washed with H2O (40 mL), a 1N NaOH solution (40 mL), H2O (40 mL) and a saturated NaCl solution (40 mL), dried (Na2SO4), and concentrated under reduced pressure. The resulting powder was purified by crystalization (EtOAc) to give 2-n-propylacetanilide as white needles (7.85 g, 67%). TLC (30% EtOAc/hex) Rf0.37.

Workup

  1. extractionThe acidic mixture was extracted with CH2Cl2 (2×30 mL)
  2. washThe combined organic layers were sequentially washed with H2O (40 mL)
  3. dry with materiala 1N NaOH solution (40 mL), H2O (40 mL) and a saturated NaCl solution (40 mL), dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting powder was purified by crystalization (EtOAc)

Sources & evidence

ORD record
ord-33cdbdd5b0e24d02959954a90fb89064
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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