Diisopropylethylamine → HCID 86606414, compound

HRID 491577Notes

Reaction equation

HRID 491577 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([C:10](Cl)=[O:11])=[N:8][N:7]([CH3:13])[N:6]=1)=[O:4].C(N(C(C)C)C(C)C)C>C1COCC1.C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:9]([CH:10]=[O:11])=[N:8][N:7]([CH3:13])[N:6]=1)=[O:4]

Participants

6

Reactant 2

HCID 81531DiisopropylethylamineHCID 86606415HCID 86606415, compound

Product 1

HCID 86606414HCID 86606414, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of freshly prepared 5-Chlorocarbonyl-2-methyl-2H-1,2,3-triazole-4-carboxylic acid methyl ester (2.7 g; ca. 13 mmol) in THF (270 ml) was added ethyl-diisopropyl-amine (1.88 g; 1.1 eq.). The mixture was hydrogenated in the presence of 2.7 g 10% Pd/C at 0-5° C. at normal pressure for 2½ hours and subsequently filtered from the catalyst. The clear solution was evaporated to give the crude as a solid which was dissolved again in ethyl acetate and stirred for a couple of minutes with silica gel. After filtration and evaporation 1.77 g (84%) of pure product as off-white crystals were obtained [m.p. 107-108° C.; 1H-NMR (300 MHz, CDCl3), δ (ppm): 10.43(s,1H), 4.33(s,3H), 4.01(s,3H)].

Workup

  1. filtrationsubsequently filtered from the catalyst
  2. customThe clear solution was evaporated
  3. customto give the crude as a solid which
  4. filtrationAfter filtration
  5. customevaporation 1.77 g (84%) of pure product as off-white crystals
  6. customwere obtained [m.p. 107-108° C.; 1H-NMR (300 MHz, CDCl3), δ (ppm): 10.43(s,1H), 4.33(s,3H), 4.01(s,3H)]

Sources & evidence

ORD record
ord-23a0f32b222647a296bd872a699343d9
Source dataset
uspto-grants-2009_05
Patent number
US07531559B2

Reaction notes

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