4-Bromobenzohydrazide → HCID 19703115, compound

HRID 861422Notes

Reaction equation

HRID 861422 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.C(O[C:15](OCC)(OCC)[CH2:16][CH3:17])C>>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[O:7][C:15]([CH2:16][CH3:17])=[N:9][N:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 222194-BromobenzohydrazideHCID 66995Ethyl orthopropionate

Product 1

HCID 19703115HCID 19703115, compound

Procedure

A mixture of 4-bromobenzoic acid hydrazide (3.23 g) and triethylorthopropionate (25 ml) was heated at reflux for 7 hours. The mixture was evaporated to give a solid which was recrystallised from ethyl acetate to give 2-(4-bromphenyl)-5-ethyl-1,3,4-oxadiazole (3.65 g), as a solid, m.p. 101°-102° C.; microanalysis found: C, 47.3; H, 3.6; N, 10.9%; C10H9BrN2O requires: C, 47.5; H, 3.58; N, 11.1%; NMR(CDCl3): 1.44(3H,t), 2.96(2H,q), 7.65(2H,d) and 7.90(2h,D); m/z 253(M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 hours
  3. customThe mixture was evaporated
  4. customto give a solid which
  5. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-5c9fa93c5b8c4f3ea0e47cbeee16ad03
Source dataset
uspto-grants-1998_02
Patent number
US05714496

Reaction notes

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