Benzyl Bromide → HCID 19008945, compound

HRID 1742426Notes

Reaction equation

HRID 1742426 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][C:13](=[O:15])[CH3:14])=[CH:7][CH:6]=[CH:5]2.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOCC>[CH2:16]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][C:13](=[O:15])[CH3:14])=[CH:7][CH:6]=[CH:5]2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 79394N-(6-Hydroxy-1-naphthyl)acetamide

Product 1

HCID 19008945HCID 19008945, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(6-hydroxy-naphthalen-1-yl)-acetamide (5.72 grams, 28 mmol), benzyl bromide (4.78 grams, 28 mmol) and potassium carbonate (4.14 grams, 30 mmol) in DMF (50 mL) was stirred at room temperature for 20 hours. The reaction was diluted with ether (250 mL) and was washed with saturated aqueous NaHCO3 (2×30 mL) and saturated aqueous NaCl (2×30 mL), dried MgSO4) and concentrated in vacuo. The crude residue was azeotroped with heptane (2×100 mL) to give a colored solid. The solid was filtered and washed with hexanes to give 5.0 grams of a colorless product. 1NMR (250 MHz, CDCl3): d 7.25 (m, 11 H), 4.4 (s, 2 H), 2.16 (s, 3 H).

Workup

  1. washwas washed with saturated aqueous NaHCO3 (2×30 mL) and saturated aqueous NaCl (2×30 mL), dried MgSO4) and
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was azeotroped with heptane (2×100 mL)
  4. customto give a colored solid
  5. filtrationThe solid was filtered
  6. washwashed with hexanes

Sources & evidence

ORD record
ord-bd7185c76dfa48c3a2cf1eae134ba42a
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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