Methanol → HCID 19915229, compound

HRID 1090341Notes

Reaction equation

HRID 1090341 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([O:25][CH3:26])[CH:24]=1)[C:6]([NH:8][NH:9][C:10](=O)[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[CH:12]=1)=[O:7].O.CO>P(Cl)(Cl)(Cl)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[O:7][C:10]([C:11]3[CH:12]=[C:13]([O:19][CH3:20])[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=3)=[N:9][N:8]=2)[CH:22]=[C:23]([O:25][CH3:26])[CH:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 2674040HCID 2674040, compound

Product 1

HCID 19915229HCID 19915229, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 20.5 g (0.057 mole) of N,N'-bis(3,5-dimethoxybenzoyl)hydrazine in 125 ml of phosphorus oxychloride was heated to reflux temperature. All material dissolved after a short time and the solution was held at reflux for 1 hr. before it was cooled and slowly poured into water. The damp precipitate was stirred with 250 ml of boiling methanol before the mixture was cooled and filtered to give 16.3 g (84%) of crude 2,5-bis(3,5-dimethoxyphenyl)-1,3,4-oxadiazole, mp 167°-170° C.; Crystallization of a small sample from methanol gave mp 173°-175° C. 1H NMR(acetone-d6): 3.98 (s, 12H), 6.83 (m, 2H), 7.43 (m, 4H). Anal. Calcd. for C18H18N2O5 : C, 63.15; H, 5.30; N, 8.18. Found: C, 62.73; H, 5.34; N, 7.98.

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperature
  3. dissolutionAll material dissolved after a short time
  4. temperatureat reflux for 1 hr
  5. temperaturebefore it was cooled
  6. temperaturewas cooled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-7cdaae6a76684b9ab4ac1eccfcbbda83
Source dataset
uspto-grants-1992_01
Patent number
US05081255

Reaction notes

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