Hydrochloric Acid → HCID 15563282, compound

HRID 2368438Notes

Reaction equation

HRID 2368438 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:11][C:10]([NH:19]C(=O)C2C=CC=CC=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>CO>[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:11][C:10]([NH2:19])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57435375HCID 57435375, compound

Product 1

HCID 15563282HCID 15563282, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The crude N-(1-benzyl-5-phenyl-1H-1,2,4-triazol-3-yl)benzamide was dissolved in 5 ml of MeOH. It was stirred and treated with 5 ml of 6N HCl. It was heated at 60° C. for overnight. It was cooled to rt and added to a stirred 4N NaOH (10 ml) in an ice bath. It was extracted with DCM. The combined DCM layer was dried with MgSO4 and rotavapped. The crude was purified by column chromatography with heptane/EtOAc gradient to yield 1-benzyl-5-phenyl-1H-1,2,4-triazol-3-amine (340 mg, 45.3% for 3 steps). 1H NMR (400 MHz, MeOD) 5.24 (br. s., 2H) 7.13 (br. s., 2H) 7.30 (br. s., 4H) 7.52 (br. s., 6H), LCMS method A, (M+H)+ 251.1, ret T=1.12 min.

Workup

  1. temperatureIt was cooled to rt
  2. extractionIt was extracted with DCM
  3. dry with materialThe combined DCM layer was dried with MgSO4
  4. customThe crude was purified by column chromatography with heptane/EtOAc gradient

Sources & evidence

ORD record
ord-d843c61e894841c9a82004c77bfb59d8
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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