Ethanol → HCID 22471857, compound

HRID 1004653Notes

Reaction equation

HRID 1004653 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][N:10]2[C:14](=[O:15])[N:13]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[N:12]=[N:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C>[Pd].C(OCC)(=O)C>[NH2:22][C:19]1[CH:18]=[CH:17][C:16]([N:13]2[C:14](=[O:15])[N:10]([CH2:9][CH2:8][CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[N:11]=[N:12]2)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 22471696HCID 22471696, compound

Product 1

HCID 22471857HCID 22471857, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(3-cyclohexyl-propyl)-4-(4-nitro-phenyl)-1,4-dihydro-tetrazol-5-one (69.6 g, 210 mmol) in a mixture of absolute ethanol (220 mL) and ethyl acetate (300 mL) was added to a 2 L Parr hydrogenation vessel containing Degussa 10% Pd/C (3.48 g). The Parr vessel was shaken at room temperature under a hydrogen atmosphere maintained at 20 psi for 4.5 hours. The mixture was filtered through Celite and concentrated in vacuo to a light yellow oil which spontaneously crystallized to afford a light brown crystalline solid (63.5 g, 98%). Mp 64-69° C.; 1H NMR (CDCl3, 300 MHz) δ 7.64 (d, 8.8 Hz, 2 H), 6.78 (d, 9.2 Hz, 2 H), 3.98 (t, 7.0 Hz, 2 H), 1.88 (m, 2 H), 1.72-1.63 (m, 5 H), 1.29-1.11 (m, 6 H), 0.94-0.84 (m, 2 H); MS (EI) m/z 302.2 (MH+); Anal. calcd for C16H23N5O: C, 63.76; H, 7.69; N, 23.24. Found: C, 64.00; H, 7.78; N, 22.87; Rf =0.67 (B).

Workup

  1. additionwas added to a 2 L Parr hydrogenation vessel
  2. temperaturemaintained at 20 psi for 4.5 hours
  3. filtrationThe mixture was filtered through Celite
  4. concentrationconcentrated in vacuo to a light yellow oil which
  5. customspontaneously crystallized

Sources & evidence

ORD record
ord-884c8d40fd634bec8840eecfafcdb0e2
Source dataset
uspto-grants-2000_04
Patent number
US06051586

Reaction notes

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