Hydrochloric Acid → HCID 19085362, compound

HRID 963035Notes

Reaction equation

HRID 963035 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][CH3:24])=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1.Cl.C(=O)([O-])[OH:27].[Na+].[Cl:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[Cl:41])[C:35](Cl)=[O:36]>C(Cl)(Cl)Cl>[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][CH3:24])=[N:21][N:22]=[C:11]1[CH2:10][NH:9][C:35](=[O:36])[C:34]1[CH:38]=[CH:39][C:40]([Cl:41])=[C:32]([Cl:31])[CH:33]=1)=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 516892Sodium BicarbonateHCID 12434326HCID 12434326, compound

Product 1

HCID 19085362HCID 19085362, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

4-(2-Chlorophenyl)-2,9-diethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (1.8 g) was added to 2.5% hydrochloric acid (35 ml), and the mixture was stirred at 60° C. overnight. Then, sodium hydrogencarbonate was added to the reaction mixture to make the mixture alkaline. Chloroform (40 ml) and 3,4-dichlorobenzoyl chloride (1.15 g) were added, and the mixture was stirred at room temperature for 2 hours. Then, the organic layer was washed with an aqueous citric acid solution and saturated brine, and dried over magnesium sulfate. After the solvent was evaporated, the residue was purified by silica gel column chromatography (developing solvent:ethyl acetate) and recrystallized from ethyl acetate to give 0.73 g of N-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-ethyl[1,2,4]triazol-3-ylmethyl)-3,4-dichlorobenzamide.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. washThen, the organic layer was washed with an aqueous citric acid solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter the solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (developing solvent:ethyl acetate)
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8dbd5e0ee84240d786012d441cf3fa36
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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