Benzenecarboximidic acid, ethyl ester, hydrochloride (1:1) → HCID 16722532, compound

HRID 1983081Notes

Reaction equation

HRID 1983081 reaction equation
Cl.[C:2](=N)(OCC)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O-]CC.[Na+].[CH3:17][C:18]1[O:22][N:21]=[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19]=1[C:29]([NH:31][NH2:32])=[O:30]>C(O)C.O1CCOCC1>[CH3:17][C:18]1[O:22][N:21]=[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19]=1[C:29]1[O:30][C:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[N:32][N:31]=1

Participants

6

Reactant 3

HCID 79249Benzenecarboximidic acid, ethyl ester, hydrochloride (1:1)HCID 7279245-Methyl-3-phenyl-4-isoxazolecarbohydrazideHCID 2723922Sodium ethoxide

Product 1

HCID 16722532HCID 16722532, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of ethyl benzimidate hydrochloride (376 mg; 2.03 mmol) in ethanol (4 mL) was added at 0° C. sodium ethoxide (2.72 M in ethanol, 355 □L, 0.99 mmol) and stirred for 15 min. The suspension was filtered off and 5-methyl-3-phenyl-isoxazole-4-carboxylic acid hydrazide (200 mg, 0.92 mmol) was added and stirred for 90 h at 70° C. The reaction mixture was suspended in dioxane (4 mL) and heated in the microwave for 30 min at 180° C. Concentration and then purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40) afforded the title compound (163 mg, 29%) as a white solid. MS: m/e=304.2 [M+H]+.

Workup

  1. filtrationThe suspension was filtered off
  2. stirringstirred for 90 h at 70° C
  3. concentrationConcentration
  4. custompurification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40)

Sources & evidence

ORD record
ord-593f269607994f9ca762e99580f58b38
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Reaction notes

Loading…