Phenol → N-[4-(phenoxymethyl)-1,3-thiazol-2-yl]acetamide

HRID 2218528Notes

Reaction equation

HRID 2218528 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:11][C:12]1[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=1>C1COCC1.C(O)C>[O:9]([CH2:11][C:12]1[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 819632-Acetamido-4-chloromethylthiazole

Product 1

HCID 2940526N-[4-(phenoxymethyl)-1,3-thiazol-2-yl]acetamideYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of sodium hydride (55 mg, 60% dispersion in mineral oil, 1.38 mmol) in THF (1 ml) at 0° C. was added phenol (100 mg, 1.06 mmol). After stirred at 0° C. for 10 minutes, the reaction solution was warmed to room temperature and stirred for 10 minutes. The reaction solution was cooled to 0° C. again, and was added a solution of N-(4-(chloromethyl)thiazol-2-yl)acetamide in ethanol (1 ml). The reaction was stirred at room temperature overnight and then was heated at 70° C. for 5 hours. The reaction solution was concentrated and the residue was purified via preparative HPLC to afford N-(4-phenoxymethyl-thiazol-2-yl)-acetamide as a tan amorphous solid (50 mg, 20%). LC/MS m/z 249.15 (M-1)+; HPLC Rt: 2.875 min.

Workup

  1. temperaturethe reaction solution was warmed to room temperature
  2. stirringstirred for 10 minutes
  3. temperatureThe reaction solution was cooled to 0° C. again
  4. stirringThe reaction was stirred at room temperature overnight
  5. temperaturewas heated at 70° C. for 5 hours
  6. concentrationThe reaction solution was concentrated
  7. customthe residue was purified via preparative HPLC

Sources & evidence

ORD record
ord-81d37d395d164dcc804244d219c47d99
Source dataset
uspto-grants-2008_08
Patent number
US07411071B2

Reaction notes

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