Water → Hydrochloric Acid

HRID 491895Notes

Reaction equation

HRID 491895 reaction equation
[CH:1]1([NH:7][C:8]([C:10]2[N:14]=[CH:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:11]=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].O.O(Cl)[Cl:46]>>[CH2:15]([N:12]1[CH:13]=[N:14][C:10]([CH2:8][NH:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:11]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1.[ClH:46]

Participants

7

Reactant 5

HCID 962WaterHCID 24646Chlorine monoxideHCID 2724148Sodium potassium tartrate tetrahydrateHCID 21226445Aluminium lithium hydrideHCID 670235851-benzyl-1H-[1,2,4]triazole-3-carboxylic acid cyclohexylamide

Product 2

HCID 313Hydrochloric AcidHCID 67023661(1-benzyl-1H-[1,2,4]triazol-3-ylmethyl)-cyclohexyl-amine

Conditions

Temperature
0 °C

Procedure

A solution of 1-benzyl-1H-[1,2,4]triazole-3-carboxylic acid cyclohexylamide (3.63 g, 12.8 mmol) in phosphosphorus oxychloride (10 mL) was heated at 70° C. for 4 hours. The solution was then concentrated. Toluene was added and then evaporated. The residue was dissolved in THF (100 mL). The solution was cooled to 0° C., and LiAlH4 (1.0 M in THF, 25.6 mL, 25.6 mmol) was added slowly into the solution. The solution was allowed to return to room temperature and then stirred for 1 hour. Potassium sodium tartrate tetrahydrate (5 g) was added. Water was added slowly to terminate the reaction. The solution was filtered and ethyl acetate was used to wash the filter cake. The filtrate was concentrated. HCl (1.0 M) in diethyl ether was added. The resulting precipitate was collected and recrystallized from acetone/methanol to yield (1-benzyl-1H-[1,2,4]triazol-3-ylmethyl)-cyclohexyl-amine as its corresponding hydrochloric acid salt, as a white solid.

Workup

  1. concentrationThe solution was then concentrated
  2. additionToluene was added
  3. customevaporated
  4. dissolutionThe residue was dissolved in THF (100 mL)
  5. customto return to room temperature
  6. customto terminate
  7. customthe reaction
  8. filtrationThe solution was filtered
  9. washto wash the filter cake
  10. concentrationThe filtrate was concentrated
  11. additionHCl (1.0 M) in diethyl ether was added
  12. customThe resulting precipitate was collected
  13. customrecrystallized from acetone/methanol

Sources & evidence

ORD record
ord-420fc4034f9d46789a6038938521cdef
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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