Potassium Carbonate → 2-Aminobenzoxazole

HRID 249822

Reaction equation

HRID 249822 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C([O-])([O-])=O.[K+].[K+].[N:17]12CCCNC1CCCC=C2.[H-].[Na+]>C1COCC1.CN(C=O)C.COCCOC.C(N(CC)CC)C>[NH2:17][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 119862-ChlorobenzoxazoleHCID 24758Sodium hydrideHCID 98128211,8-Diazabicyclo[5.4.0]undec-2-ene

Product 1

HCID 207072-Aminobenzoxazole

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of an appropriate 2-chlorobenzoxazole, A1 (1 eq), and appropriate amine (2 eq) and optional base (e.g. K2CO3, triethylamine, disopropylamine, 1,8-diazabicyclo[5.4.0]undecene, or sodium hydride) in THF (or DME, DMF) was heated in the range of 20 to 80° C. up to 24 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (typical eluents include 9:1 dichloromethane/methanol, ethyl acetate, hexanes) to afford the desired product 2-aminobenzoxazole. Product structure was confirmed by 1H NMR or by mass analysis.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe crude product was purified by silica gel column chromatography (typical eluents include 9:1 dichloromethane/methanol, ethyl acetate, hexanes)

Sources & evidence

ORD record
ord-2ed551dac8ad4c8da588727013cf15c2
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Linked notes

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