Triethylamine → HCID 25104413, compound

HRID 1951036Notes

Reaction equation

HRID 1951036 reaction equation
[CH3:1][N:2]([CH:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1)[C:3]([C:5]1[CH:13]=[CH:12][C:8]2=[N:9][O:10][N:11]=[C:7]2[CH:6]=1)=[O:4].Cl.[O:22]([NH2:24])[CH3:23].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:23][O:22][N:24]=[C:17]1[CH2:18][CH2:19][CH:14]([N:2]([CH3:1])[C:3]([C:5]2[CH:13]=[CH:12][C:8]3=[N:9][O:10][N:11]=[C:7]3[CH:6]=2)=[O:4])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 25103068HCID 25103068, compound

Product 1

HCID 25104413HCID 25104413, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-Methyl-N-(4-oxocyclohexyl)-[2,1,3]-benzoxadiazole-5-carboxamide (0.41 g, 1.5 mmol) was dissolved in chloroform (10 ml), methoxylamine hydrochloride (0.75 g) and triethylamine (1.6 ml) were added, and the mixture stirred overnight. Evaporation of the solvent and chromatography of the residue on silica gel, eluting with chloroform/ethyl acetate (3:2), gave a white solid (0.32 g). Mp=167-168° C., 1H NMR (300 MHz, CDCl3) δ 7.93 (d, J=9.3 Hz, 1H); 7.84 (m, 1H); 7.42 (d, J=9.3 Hz, 1H); 4.85-4.70 and 3.80-3.30 (m, 1H); 3.83 (s, 3H); 2.99 and 2.88 (s+s, 3H); 2.60-1.60 ppm (s, 8H).

Workup

  1. customEvaporation of the solvent and chromatography of the residue on silica gel
  2. washeluting with chloroform/ethyl acetate (3:2)

Sources & evidence

ORD record
ord-805f2aa291d74ce78ce32e6c77a5ac46
Source dataset
uspto-grants-2013_03
Patent number
US08404682B2

Reaction notes

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