Sulfuric Acid → HCID 18917664, compound

HRID 1291747Notes

Reaction equation

HRID 1291747 reaction equation
N1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=N1.C1(C2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]3[C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[N:26][N:27]=[C:17]3[CH2:16]N=2)C=CC=CC=1.S(=O)(=O)(O)O.N([O-])=O.[Na+].C(=O)([O-])[O-:49].[K+].[K+].[O:54]1[CH2:59][CH2:58]OCC1>O>[OH:49][CH2:16][C:17]1[N:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=2[C:59]([C:58]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:54])[C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[N:26][N:27]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 23668193Sodium NitriteHCID 86752604HCID 86752604, compound

Product 1

HCID 18917664HCID 18917664, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

6-Phenyl-1-undecyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine diazepine (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-undecyl-1,2,4-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-bc11a3c9d745471ba957c9eeb6361ef2
Source dataset
uspto-grants-1998_05
Patent number
US05753649

Reaction notes

Loading…