Water → HCID 18917609, compound

HRID 234053Notes

Reaction equation

HRID 234053 reaction equation
[CH2:1]([C:3]1[S:12][C:11]2[N:10]3[C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[N:14][N:15]=[C:9]3[CH2:8]N=[C:6]([C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)[C:5]=2[CH:4]=1)[CH3:2].S(=O)(=O)(O)[OH:35].N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].[OH2:49]>O1CCOCC1>[CH2:1]([C:3]1[S:12][C:11]([N:10]2[C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[N:14][N:15]=[C:9]2[CH2:8][OH:49])=[C:5]([C:6](=[O:35])[C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)[CH:4]=1)[CH3:2]

Participants

7

Reactant 5

HCID 962Water2×HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 135667574HCID 135667574, compound

Product 1

HCID 18917609HCID 18917609, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

2-Ethyl-4-(4-hydroxyphenyl)-9-undecyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (20 g) obtained in Example 17 was dissolved in dioxane (300 ml). Thereto were added water (300 ml) and sulfuric acid (12 ml) and the mixture was stirred at 80° C. for 2 hours. Thereto was gradually added dropwise a solution of sodium nitrite (30 g) in water (100 ml) and the mixture was stirred at 80° C. for 3 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 purified by silica gel column chromatography to give 11 g of 5-ethyl-3-(4-hydroxybenzoyl)-2-(3-hydroxymethyl-5-undecyl1,2,4-triazol-4-yl)thiophene as an oily substance.

Workup

  1. stirringthe mixture was stirred at 80° C. for 3 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. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-c49fcae2d4e7488fb5be30bf292ab316
Source dataset
uspto-grants-1997_01
Patent number
US05593988

Reaction notes

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