Water → [5-(4-Methoxyphenyl)-1,2,4-oxadiazol-3-yl]methanamine

HRID 2246847Notes

Reaction equation

HRID 2246847 reaction equation
Cl[CH2:2][C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[O:5][N:4]=1.[N-:16]=[N+]=[N-].[Na+].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[O:5][N:4]=[C:3]([CH2:2][NH2:16])[N:7]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 27971313-(Chloromethyl)-5-(4-methoxyphenyl)-1,2,4-oxadiazole

Product 1

HCID 17604973[5-(4-Methoxyphenyl)-1,2,4-oxadiazol-3-yl]methanamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-chloromethyl-5-(4-methoxy-phenyl)-[1,2,4]oxadiazole (8.90 mmol) in N,N-dimethylformamide (10 mL) was added sodium azide (17.8 mmol). This mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into water (30 mL) and extracted with dichloromethane (3×). The combined organic extracts were combined and washed with water (2×), dried over anhydrous sodium sulfate, and evaporated. Then clear oily residue was placed under high vacuum and gently warmed for 18 hours. Upon cooling the material solidified. This solid was dissolved in tetrahydrofuran (15 mL) and treated with triphenylphosphine (9.0 mmol). Bubbling was immediately evident. This mixture was stirred for 16 hours and then treated with water (3.0 mL). This was heated in a 45° C. oil bath for 3 hours. The product was purified by flash chromatography (silica gel; 2:1 ether/dichloromethane), m.p. 66-68° C.

Workup

  1. extractionextracted with dichloromethane (3×)
  2. washwashed with water (2×)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. temperaturegently warmed for 18 hours
  6. temperatureUpon cooling the material solidified
  7. dissolutionThis solid was dissolved in tetrahydrofuran (15 mL)
  8. customBubbling
  9. stirringThis mixture was stirred for 16 hours
  10. additiontreated with water (3.0 mL)
  11. temperatureThis was heated in a 45° C. oil bath for 3 hours
  12. customThe product was purified by flash chromatography (silica gel; 2:1 ether/dichloromethane), m.p. 66-68° C.

Sources & evidence

ORD record
ord-99e15b2aceb54e018d6ce54015e74750
Source dataset
uspto-grants-2010_03
Patent number
US07687623B2

Reaction notes

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