2-Bromoacetyl-6-methoxynaphthalene → HCID 68984203, compound

HRID 1820837Notes

Reaction equation

HRID 1820837 reaction equation
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:11][C:12]([C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH:20]=2)[CH:15]=1)=O>C(O)C>[CH3:25][O:24][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:12]1[N:9]=[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[S:8][CH:11]=1)[CH:23]=[CH:22]2

Participants

4

Reactant 2

HCID 1934522-Bromoacetyl-6-methoxynaphthaleneHCID 683563Thiobenzamide

Product 1

HCID 68984203HCID 68984203, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiobenzamide (447 mg, 3.26 mmol) was added under nitrogen to a solution of (2-bromo-1-(6-methoxy-2-naphthyl)ethanone (906 mg, 3.25 mmol), prepared in the previous step, in 25 mL of absolute ethanol at approximately 70° C. After the addition the reaction was refluxed for 2 h. The solid was collected by filtration, rinsed with absolute ethanol and dried under reduced pressure to give 4-(6-methoxy-2-naphthyl)-2-phenyl-1,3-thiazole (909 mg, 88%) as a white solid, mp 191-193° C. Elemental Analysis for C20H15NOS Calc'd: C, 75.68; H, 4.76; N, 4.41. Found: C, 75.37; H, 4.65; N, 4.31.

Workup

  1. additionAfter the addition the reaction
  2. temperaturewas refluxed for 2 h
  3. filtrationThe solid was collected by filtration
  4. washrinsed with absolute ethanol
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-671a37ab098f4a5891058dad5542044e
Source dataset
uspto-grants-2009_10
Patent number
US07605172B2

Reaction notes

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