Oxalic Acid → HCID 68708571, compound

HRID 216008Notes

Reaction equation

HRID 216008 reaction equation
[C:1]1([C:7]2[CH:11]=[N:10][N:9]([CH2:12][CH2:13][N:14]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23]>CCOCC.CCOC(C)=O>[C:21]([O-:26])(=[O:25])[C:22]([O-:24])=[O:23].[C:1]1([C:7]2[CH:11]=[N:10][N:9]([CH2:12][CH2:13][NH+:14]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]1([C:7]2[CH:11]=[N:10][N:9]([CH2:12][CH2:13][NH+:14]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 25015796HCID 25015796, compound2×

Product 1

HCID 68708571HCID 68708571, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[2-(4-Phenyl-[1,2,3]triazol-2-yl)-ethyl]azepane (compound 22) (0.25 mmol) was dissolved in ether (0.5 mL) and mixed with a solution of oxalic acid (0.25 mmol) in AcOEt (0.1 mL) to give 1-[2-(4-Phenyl-[1,2,3]triazol-2-yl)-ethyl]azepanium oxalate as a white precipitate which was filtered off and dried in vacuum. 1H NMR (500 MHz, DMSOd6, 25° C.) δ=8.32 (1H, s), 7.85 (2H, d, 3J=7.4 Hz), 7.47 (2H, t, 3J=7.4 Hz), 7.38 (1H, t, 3J=7.4 Hz), 4.78 (2H, t, 3J=6.2 Hz), 3.52 (2H, sw), 3.09 (4H, sw), 1.70 (4H, sw), 1.55 (4H, sw) ppm. ES-MS m/z=271.0; C18H24N4O4×½ H2O (369.4): caldc. C, 58.52; H, 6.82; N, 15.17. found C, 58.08; H, 6.61; N, 14.71.

Sources & evidence

ORD record
ord-eda758179d2c418d986fb46a8cf74444
Source dataset
uspto-grants-2012_06
Patent number
US08193223B2

Reaction notes

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