Chloroform → HCID 19085262, compound

HRID 963079Notes

Reaction equation

HRID 963079 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][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:22][CH:21]=3)[S:17][C:13]=2[N:12]2[C:30]([CH3:33])=[N:31][N:32]=[C:11]2[CH2:10][N:9]=1.C(=O)([O-])[OH:35].[Na+].C(Cl)(Cl)Cl.[Cl:43][C:44]1[CH:45]=[C:46]([CH:50]=[CH:51][C:52]=1[Cl:53])[C:47](Cl)=[O:48]>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][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:22][CH:21]=2)[S:17][C:13]=1[N:12]1[C:30]([CH3:33])=[N:31][N:32]=[C:11]1[CH2:10][NH:9][C:47](=[O:48])[C:46]1[CH:50]=[CH:51][C:52]([Cl:53])=[C:44]([Cl:43])[CH:45]=1)=[O:35]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 516892Sodium BicarbonateHCID 10695884HCID 10695884, compound

Product 1

HCID 19085262HCID 19085262, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

4-(2-Chlorophenyl)-2-(2-(4-isobutylphenyl)ethyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine described in Example 1 of Japanese Patent Publication No. 55510/1993 was dissolved in a 5% aqueous hydrochloric acid solution, and the solution was stirred at 60° C. for 5 hours. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture to make the mixture alkaline. Chloroform and 3,4-dichlorobenzoyl chloride were added, and the mixture was stirred under ice-cooling for 1 hour. 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 purified to give N-(4-(3-(2-chlorobenzoyl)-5-(2-(4-isobutylphenyl)ethyl)thiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethyl)-3,4-dichlorobenzamide.

Workup

  1. stirringthe mixture was stirred under ice-
  2. temperaturecooling for 1 hour
  3. washThe 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 purified

Sources & evidence

ORD record
ord-543ebe556d1d428cb126fbc168295078
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

Loading…