Sulfuric Acid → HCID 19085233, compound

HRID 963057Notes

Reaction equation

HRID 963057 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH3:19])[S:17][C:13]=2[N:12]2[C:20]([CH2:23][NH:24][C:25](=[O:34])[C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=3)=[N:21][N:22]=[C:11]2CN=1.S(=O)(=O)(O)O.N([O-])=[O:41].[Na+].[C:44](=[O:47])([O-])O.[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:14]1[CH:15]=[C:16]([CH2:18][CH3:19])[S:17][C:13]=1[N:12]1[C:20]([CH2:23][NH:24][C:25](=[O:34])[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)=[N:21][N:22]=[C:11]1[CH2:44][OH:47])=[O:41]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 67727741HCID 67727741, compound

Product 1

HCID 19085233HCID 19085233, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Water (20 ml) and dioxane (20 ml) were added to N-(4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-9-ylmethyl)-3,4-dichlorobenzamide (3.0 g), and conc. sulfuric acid (1.2 ml) was dropwise added with vigorous stirring. Then, the mixture was stirred at 80° C. for 1.5 hours. Sodium nitrite (3.9 g) was added, and the mixture was further stirred for 1 hour. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (developing solvent:ethyl acetate) and recrystallized from a mixed solvent of ethyl acetate-hexane to give 0.9 g of N-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-3-hydroxymethyl[1,2,4]triazol-5-ylmethyl)-3,4-dichlorobenzamide.

Workup

  1. additionwas dropwise added with vigorous stirring
  2. stirringthe mixture was further stirred for 1 hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography (developing solvent:ethyl acetate)
  7. customrecrystallized from a mixed solvent of ethyl acetate-hexane

Sources & evidence

ORD record
ord-a353205b05ec4a58bf3b89197bbb4bf0
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

Loading…