Hydrochloric Acid → HCID 67727746, compound

HRID 963041Notes

Reaction equation

HRID 963041 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][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1.Cl.C(=O)([O-])[OH:32].[Na+].[Cl:36][C:37]1[CH:38]=[C:39]([CH:43]=[CH:44][C:45]=1[Cl:46])[C:40](Cl)=[O:41]>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][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:21][N:22]=[C:11]1[CH2:10][NH:9][C:40](=[O:41])[C:39]1[CH:43]=[CH:44][C:45]([Cl:46])=[C:37]([Cl:36])[CH:38]=1)=[O:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 516892Sodium BicarbonateHCID 67727694HCID 67727694, compound

Product 1

HCID 67727746HCID 67727746, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

4-(2-Chlorophenyl)-9-(2-ethoxycarbonylethyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (3.3 g) was added to 5% hydrochloric acid (35 ml), and the mixture was stirred at 40° C. for 4 hours. Then, sodium hydrogencarbonate was added to the reaction mixture to make the mixture alkaline. Chloroform (50 ml) and 3,4-dichlorobenzoyl chloride (1.61 g) were added under ice-cooling, and the mixture was allowed to stand overnight. Then, the organic layer was taken out, washed with an aqueous citric acid solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (developing solvent:ethyl acetate-methanol) and recrystallized from ethyl acetate-hexane to give 1.08 g of ethyl 3-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-3-(3,4-dichlorobenzoylaminomethyl) [1,2,4]triazol-5-yl)propionate.

Workup

  1. temperaturecooling
  2. waitto stand overnight
  3. washwashed with an aqueous citric acid solution and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (developing solvent:ethyl acetate-methanol)
  7. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8c66431dd0ce4a3d8b1889960841ef49
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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