Hydrochloric Acid → HCID 19085375, compound

HRID 963039Notes

Reaction equation

HRID 963039 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]([C:23]([F:26])([F:25])[F:24])=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1.Cl.C(=O)([O-])[OH:29].[Na+].[Cl:33][C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][C:42]=1[Cl:43])[C:37](Cl)=[O:38]>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]([C:23]([F:26])([F:25])[F:24])=[N:21][N:22]=[C:11]1[CH2:10][NH:9][C:37](=[O:38])[C:36]1[CH:40]=[CH:41][C:42]([Cl:43])=[C:34]([Cl:33])[CH:35]=1)=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 516892Sodium BicarbonateHCID 67727704HCID 67727704, compound

Product 1

HCID 19085375HCID 19085375, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

4-(2-Chlorophenyl)-2-ethyl-9-trifluoromethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (1.0 g) was added to 10% hydrochloric acid (20 ml), and the mixture was stirred at 70° C. overnight. Then, sodium hydrogencarbonate was added to the reaction mixture to make the mixture alkaline. Chloroform (20 ml) and 3,4-dichlorobenzoyl chloride (0.58 g) were added, and the mixture was stirred under ice-cooling for 1 hour. Then, the organic layer was washed with an aqueous citric acid solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from ethyl acetate-hexane to give 0.60 g of N-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-trifluoromethyl[1,2,4]triazol-3-ylmethyl)-3,4-dichlorobenzamide.

Workup

  1. stirringthe mixture was stirred under ice-
  2. temperaturecooling for 1 hour
  3. washThen, the organic layer was washed with an aqueous citric acid solution
  4. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0653b4ec993b4abb98963960eefc6550
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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