Methanol → N-Benzylacetamide

HRID 567430Notes

Reaction equation

HRID 567430 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:16](Cl)(=[O:18])[CH3:17].CO>C(Cl)Cl>[C:16]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 6367Acetyl chlorideHCID 7504BenzylamineHCID 8471Triethylamine

Product 1

HCID 11500N-BenzylacetamideYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 g of benzylamine was dissolved in 200 ml of methylene chloride followed by the addition of 26 ml of triethylamine and dropwise addition of 7.3 ml of acetyl chloride at 0° C. After stirring for 1 hour at room temperature, 2 ml of methanol was added to the reaction system at 0° C. followed by 120 ml of water and separation of the phases. The aqueous layer was extracted with 100 ml of chloroform, and the resulting organic layer was concentrated after drying with anhydrous sodium sulfate to obtain 8.55 g of the target compound (yield: 61%).

Workup

  1. customfollowed by 120 ml of water and separation of the phases
  2. extractionThe aqueous layer was extracted with 100 ml of chloroform
  3. concentrationthe resulting organic layer was concentrated
  4. dry with materialafter drying with anhydrous sodium sulfate

Sources & evidence

ORD record
ord-32fe6c96cbd54aac947ff52b28a89bf2
Source dataset
uspto-grants-2001_01
Patent number
US06177438B1

Reaction notes

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