Water → HCID 18917588, compound

HRID 234052Notes

Reaction equation

HRID 234052 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]([O:33][CH3:34])=[CH:29][CH:28]=3)[C:5]=2[CH:4]=1)[CH3:2].S(=O)(=O)(O)[OH:36].N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].[OH2:50]>>[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:50])=[C:5]([C:6](=[O:36])[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[CH:4]=1)[CH3:2]

Participants

6

Reactant 5

HCID 962Water2×HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 18917605HCID 18917605, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 18917588HCID 18917588, compound

Conditions

Temperature
80 °C

Procedure

2-Ethyl-4-(4-methoxylphenyl)-9-undecyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (8.0 g) obtained in Example 16 was suspended in water (200 ml). Thereto was added sulfuric acid (7.6 ml) and the mixture was stirred at 80° C. for 2 hours. Thereto was gradually added dropwise a solution of sodium nitrite (7.6 g) in water (25 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 the residue was purified by silica gel column chromatography to give 4.4 g of 5-ethyl-3-(4-methoxybenzoyl)-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. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1b20bb2c7d224d77bf6d7961bbd47b27
Source dataset
uspto-grants-1997_01
Patent number
US05593988

Reaction notes

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