N'-acetylbenzohydrazide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Synthesis and isolation were same as for 1-acetyl-2-benzoylhydrazine, using 1.8 g (10.8 mmol) of 4-methoxybenzoylhydrazine, 1.2 g (11.1 mmol) of (CH3)2NCOCl, and 1.1 g of TEA. Yield was 1.5 g (59%). MS (EI, m/e) calcd for C11H15N3O3 237, found 237 (M+, 8.3); mp 218-220° C. Synthesis and isolation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Synthesis and isolation were same as for 1-acetyl-2-benzoylhydrazine, using 1.8 g (10.8 mmol) of 4-methoxybenzoylhydrazine, 1.2 g (11.1 mmol) of (CH3)2NCOCl, and 1.1 g of TEA. Yield was 1.5 g (59%). MS (EI, m/e) calcd for C11H15N3O3 237, found 237 (M+, 8.3); mp 218-220° C. Synthesis and isolation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Synthesis and isolation were same as 1-acetyl-2-benzoylhydrazine, using 1.5 g (11.2 mmol) of benzoylhydrazide, 1.9 g (11.1 mmol) of 4-methoxybenzoylchloride and 1.1 g of TEA. Yield was 2.9 g (97%). 1H NMR (200 MHz, d6-DMSO) δ 5.13 (s, 3H), 8.36 (d, 2H), 8.86 (m, 3H), 9.23 (d, 4H) 11.72 (d, 2H); MS (EI, m/e, relative intensity %) calcd for C15H14N2O3 270, found 270 (M+, 5.1); mp 201-202° C. Synthesis and isolation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Synthesis and isolation were same as 1-acetyl-2-benzoylhydrazine, using 1.5 g (11.2 mmol) of benzoylhydrazide, 1.2 g (11.2 mmol) of (CH3)2NCOCl and 1.11 g of TEA. Yield was 0.9 g (39%). 1H NMR (200 MHz, d6-DMSO) δ 2.90 (s, 6H), 7.50 (m, 3H), 7.90 (d, 3H), 8.45 (s, 1H), 10.05 (s, 1H); MS (EI, m/e, relative intensity %) calcd for C10H13N3O2 207, found 207 (M, 13.2); mp 199-201° C. Synthesis and isolation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Synthesis and isolation were same as 1-acetyl-2-benzoylhydrazine, using 1.5 g (11.2 mmol) of benzoylhydrazide, 1.2 g (11.2 mmol) of (CH3)2NCOCl and 1.11 g of TEA. Yield was 0.9 g (39%). 1H NMR (200 MHz, d6-DMSO) δ 2.90 (s, 6H), 7.50 (m, 3H), 7.90 (d, 3H), 8.45 (s, 1H), 10.05 (s, 1H); MS (EI, m/e, relative intensity %) calcd for C10H13N3O2 207, found 207 (M, 13.2); mp 199-201° C. Synthesis and isolation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Synthesis and isolation were same as 1-acetyl-2-benzoylhydrazine, using 1.5 g (11.2 mmol) of benzoylhydrazide, 1.2 g (11.2 mmol) of (CH3)2NCOCl and 1.11 g of TEA. Yield was 0.9 g (39%). 1H NMR (200 MHz, d6-DMSO) δ 2.90 (s, 6H), 7.50 (m, 3H), 7.90 (d, 3H), 8.45 (s, 1H), 10.05 (s, 1H); MS (EI, m/e, relative intensity %) calcd for C10H13N3O2 207, found 207 (M, 13.2); mp 199-201° C. Synthesis and isolation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 60% Perchloric acid (12 ml) was added to a stirred suspension of 1-acetyl-2-benzoyl hydrazine (31 g, 0.174 mole) in acetic anhydride (150 ml) over 45 minutes at 5°±5° C. The solution was brought to ambient temperature over 1 hour, then filtered. The precipitate was dissolved in water (200 ml), solid sodium carbonate added to pH 9 and the product extracted with ethyl acetate. The extract was washed with water, dried over MgSO4 and concentrated to an oil. Chromatography gave 2-methyl-5-phenyl-1,3,4-oxadiazole as a gum (9 g, 30%). This was reacted with ethanolamine following the procedure of Preparation (a) above to give the title compound as an oil (5 g). filtered The precipitate was dissolved in water (200 ml) solid sodium carbonate added to pH 9 the product extracted with ethyl acetate The extract was washed with water dried over MgSO4 concentrated to an oil