N-methoxy-N-methylbenzo[c][1,2,5]oxadiazole-5-carboxamide → HCID 45086248, compound

HRID 2173451Notes

Reaction equation

HRID 2173451 reaction equation
CON(C)[C:4]([C:6]1[CH:14]=[CH:13][C:9]2=[N:10][O:11][N:12]=[C:8]2[CH:7]=1)=[O:5].[CH3:16][Li]>C1COCC1>[N:10]1[O:11][N:12]=[C:8]2[CH:7]=[C:6]([C:4](=[O:5])[CH3:16])[CH:14]=[CH:13][C:9]=12

Participants

4

Reactant 2

HCID 59354764N-methoxy-N-methylbenzo[c][1,2,5]oxadiazole-5-carboxamideHCID 178418348HCID 178418348, compound

Product 1

HCID 45086248HCID 45086248, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-Methoxy-N-methyl-2,1,3-benzoxadiazole-5-carboxamide (630 mg, 3.04 mmol) in THF (5 mL) cooled to −40° C. was added methyl lithium solution (1.6M, 2.28 mL, 3.65 mmol). The reaction mixture was stirred at the same temperature for 1 h, then was quenched by addition of 1M HCl. The mixture was extracted with ethyl acetate and the organic layer was dried over MgSO4. Purification my flash chromatography afforded the title compound. 1H-NMR (500 MHz, CDCl3) δ ppm 8.48 (s, 1H), 8.02 (d, 1H), 7.91 (d, 1H), 2.72 (s, 3H).

Workup

  1. customwas quenched by addition of 1M HCl
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over MgSO4
  4. customPurification my flash chromatography

Sources & evidence

ORD record
ord-ee3cfcf05a0746ee9a8e0f26d8d8862d
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…