Water → HCID 18917664, compound

HRID 234055Notes

Reaction equation

HRID 234055 reaction equation
[C:1]1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]3[C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[N:19][N:20]=[C:10]3[CH2:9]N=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)[OH:33].N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].[OH2:47]>O1CCOCC1>[OH:47][CH2:9][C:10]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:33])[C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[N:19][N:20]=1

Participants

7

Reactant 5

HCID 962Water2×HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 18917603HCID 18917603, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 18917664HCID 18917664, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

6-phenyl-1-undecyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine (3.2 g) obtained in Example 19 was dissolved in dioxane (30 ml). Thereto were added water (30 ml) and sulfuric acid (2.1 ml) and the mixture was stirred at 60° C. for 1 hour. Thereto was gradually added dropwise a solution of sodium nitrite (5.5 g) in water (20 ml) and the mixture was stirred at 70° C. for 2 hours. After cooling, potassium carbonate was added thereto to make the reaction mixture alkaline. The mixture was extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to give 0.4 g of 2-(3-hydroxymethyl-5-undecyl1,2,4-triazol-4-yl)benzophenone as an oily substance, melting point 111°-112° C.

Workup

  1. stirringthe mixture was stirred at 70° C. for 2 hours
  2. temperatureAfter cooling
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a97e9c83bb214c51a6c389372ea6f8d0
Source dataset
uspto-grants-1997_01
Patent number
US05593988

Reaction notes

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