HCID 10806269, compound → HCID 18957138, compound

HRID 2379467Notes

Reaction equation

HRID 2379467 reaction equation
[CH2:1]([N:13]1[N:17]=[N:16][C:15]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:14]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>[Ru].C(O)C>[CH:19]1([NH:18][C:15]2[N:16]=[N:17][N:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[N:14]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

4

Reactant 1

HCID 10806269HCID 10806269, compound

Product 1

HCID 18957138HCID 18957138, compound

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-dodecyl-N-phenyl-2H-tetrazol-5-amine (1.54 g, 0.00467 mol) and absolute ethanol (100 mL) was hydrogenated over 10% ruthenium on carbon (0.5 g) at 1100 psi and 100° C. for 10 hours. The mixture was allowed to cool to room temperature, and the catalyst was filtered off and washed with additional ethanol (200 mL). The filtrate and washings were combined and rotoevaporated to a glaze. The glaze was triturated with diethyl ether. The organic triturate was rotoevaporated to a solid, and the solid chromatographed on silica gel (50 g, 70-230 mesh) using PET ether-acetone (10:1, 7×50 mL) as eluent. Fractions containing title compound were rotoevaporated from dichloromethane to a white solid. The solid was dried in vacuo (25° C.), yield 1.30 g (83%), mp=51°-53° C.

Workup

  1. filtrationthe catalyst was filtered off
  2. washwashed with additional ethanol (200 mL)
  3. customThe glaze was triturated with diethyl ether
  4. customThe organic triturate
  5. customthe solid chromatographed on silica gel (50 g, 70-230 mesh)
  6. additionFractions containing title compound
  7. customThe solid was dried in vacuo (25° C.), yield 1.30 g (83%), mp=51°-53° C.

Sources & evidence

ORD record
ord-4a8e9330ae9c4ca1b5e21b885ded6c61
Source dataset
uspto-grants-1994_11
Patent number
US05362744

Reaction notes

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