2-Naphthol → HCID 178419960, compound

HRID 744075Notes

Reaction equation

HRID 744075 reaction equation
[H-].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[OH:13].Cl.Cl[CH2:16][CH2:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[O:13][CH2:16][CH2:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1

Participants

6

Reactant 3

HCID 86632-NaphtholHCID 24758Sodium hydrideHCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Product 1

HCID 178419960HCID 178419960, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

240 mg (60% in oil, 6 mmol) of sodium hydride are added to a solution of 1.73 g (12 mmol) of 2-naphthol in 10 ml of dimethylformamide. The mixture is stirred at room temperature for 3 hours under nitrogen. 200 mg (1.2 mmol) of 4-(2-chloroethyl)-1H-imidazole hydrochloride and tetrabutylammonium iodide (catalytic amount) are added and the mixture is heated at 100° C. for 3 days and then the solvent is evaporated under reduced pressure. The excess 2-naphthol is extracted with diethyl ether under acidic conditions (dilute hydrochloric acid). The aqueous solution is basified with potassium carbonate and the product is extracted with diethyl ether. The ethereal extracts are concentrated and the residue obtained is crystallized from a methanol/water (1/2) mixture, M.p.: 157°-158° C.

Workup

  1. temperaturethe mixture is heated at 100° C. for 3 days
  2. customthe solvent is evaporated under reduced pressure
  3. extractionThe excess 2-naphthol is extracted with diethyl ether under acidic conditions (dilute hydrochloric acid)
  4. extractionthe product is extracted with diethyl ether
  5. concentrationThe ethereal extracts are concentrated
  6. customthe residue obtained
  7. customis crystallized from a methanol/water (1/2) mixture, M.p.: 157°-158° C.

Sources & evidence

ORD record
ord-3cb0a6774a13492bad71a5ae338e282b
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

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