Triethylamine → HCID 25104412, compound

HRID 238552Notes

Reaction equation

HRID 238552 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.[NH2:22][OH:23].C(N(CC)CC)C>C(Cl)(Cl)Cl>[OH:23][N:22]=[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 443297Hydroxyamine hydrochlorideHCID 25103068HCID 25103068, compound

Product 1

HCID 25104412HCID 25104412, compoundYield 85.6%

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), hydroxylamine hydrochloride (0.63 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 (0.37 g). Mp=197-198° C., 1H NMR (300 MHz, CDCl3) δ 8.49 (s, 1H); 7.93 (d, J=9.0 Hz, 1H); 7.86 (m, 1H); 7.43 (d, J=9.0 Hz, 1H); 4.90-4.70 and 3.80-3.35 (m, 1H); 2.99 and 2.88 (s+s, 3H); 2.80-1.50 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-0c56b291280043b0ad8f98abb9c14a9e
Source dataset
uspto-grants-2014_02
Patent number
US08642633B2

Reaction notes

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