Water → HCID 18917678, compound

HRID 234054Notes

Reaction equation

HRID 234054 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][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[N:14][N:15]=[C:9]3[CH2:8]N=[C:6]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)[C:5]=2[CH:4]=1)[CH3:2].S(=O)(=O)(O)[OH:41].N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].[OH2:55]>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][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[N:14][N:15]=[C:9]2[CH2:8][OH:55])=[C:5]([C:6](=[O:41])[C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)[CH:4]=1)[CH3:2]

Participants

7

Reactant 5

HCID 962Water2×HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 18917587HCID 18917587, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 18917678HCID 18917678, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

2-Ethyl-9-heptadecyl-4-(4-methylphenyl)-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (6 g) obtained in Example 18 was dissolved in dioxane (60 ml). Thereto were added water (60 ml) and sulfuric acid (2.9 ml) and the mixture was stirred at 80° C. for 2 hours. A solution of sodium nitrite (7.6 g) in water (25 ml) was gradually added dropwise 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 the residue was purified by silica gel column chromatography. The oily substance obtained was crystallized from hexane to give 0.6 g of 5-ethyl-3-(4-methylbenzoyl)-2-(5-heptadecyl-3-hydroxymethyl-1,2,4-triazol-4-yl)thiophene as white crystals, melting point 68°-69° C.

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. customthe residue was purified by silica gel column chromatography
  9. customThe oily substance obtained
  10. customwas crystallized from hexane

Sources & evidence

ORD record
ord-6962e304202e4441b0a2cc2366e63a46
Source dataset
uspto-grants-1997_01
Patent number
US05593988

Reaction notes

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