N'-(4-iodobenzoyl)-3-methoxybenzohydrazide → 2-(4-Iodophenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole

HRID 2278460Notes

Reaction equation

HRID 2278460 reaction equation
[I:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][NH:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=O)=[CH:4][CH:3]=1>O=P(Cl)(Cl)Cl>[I:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]2[O:19][C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)=[N:9][N:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 67510202N'-(4-iodobenzoyl)-3-methoxybenzohydrazide

Product 1

HCID 675102152-(4-Iodophenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

N′-(4-iodobenzoyl)-3-methoxybenzohydrazide (7.0 g, 17.67 mmol) was suspended in POCl3 (40.0 ml) and heating was started. The reaction was kept at 100° C. During heating white solid of starting materials dissolved into a clear solution and the reaction was monitor by thin layer chromatography. After 1 h, the reaction mixture was brought to room temperature and was carefully dropped into ice-water (500.0 ml). White solid precipitated out was collected by filtration and washed with water. After dry, the crude product was purified by silica gel column chromatography eluting with dichloromethane and ethyl acetate in 25:1 ratio. After evaporating solvent the white solid was recrystallized from acetone/water and finally dried under vacuum. Pure product was obtained as white solid in 5.8 g (86.8%) yield. 1H NMR (400 MHz, CDCl3, δ): 7.86 (d, J=8.4 Hz, 2H), 7.83 (d, J=8.4 Hz, 2H), 7.67 (dt, J1=8.0 Hz, J2=1.2 Hz, 1H), 7.63 (m, 1H), 7.42 (t, J=8 Hz, 1H), 7.07 (m, 1H), 3.88 (s, 3H, OCH3). 13C NMR (100 MHz, CDCl3, δ): 164.66, 164.00, 159.92, 138.32, 130.23, 128.21, 124.73, 123.26, 119.29, 118.26, 111.56, 98.60, 55.52.

Workup

  1. temperatureheating
  2. customwas kept at 100° C
  3. temperatureDuring heating white solid of starting materials
  4. dissolutiondissolved into a clear solution
  5. customwas brought to room temperature
  6. customWhite solid precipitated out
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customAfter dry
  10. customthe crude product was purified by silica gel column chromatography
  11. washeluting with dichloromethane and ethyl acetate in 25:1 ratio
  12. customAfter evaporating solvent the white solid
  13. customwas recrystallized from acetone/water
  14. customfinally dried under vacuum
  15. customPure product was obtained as white solid in 5.8 g (86.8%)
  16. customyield

Sources & evidence

ORD record
ord-ca2e08461b194fb3b00b09313f9f24e7
Source dataset
uspto-grants-2015_09
Patent number
US09133177B2

Reaction notes

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