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Hydrochloric Acid → N-(3-chloro-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl) [1,2,4]triazol-5-ylmethyl)indole-2-carboxamide

HRID 963096
Notes
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Reaction equation

HRID 963096 reaction equation
[Cl:1][C:2]1[N:6]2[C:7]3[S:21][C:20]([CH2:22][CH3:23])=[CH:19][C:8]=3[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])=[N:10][CH2:11][C:5]2=[N:4][N:3]=1.Cl.C(=O)([O-])[OH:26].[Na+].[NH:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[C:31]1[C:39](Cl)=[O:40]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:6]([C:7]2[S:21][C:20]([CH2:22][CH3:23])=[CH:19][C:8]=2[C:9](=[O:26])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[C:5]([CH2:11][NH:10][C:39]([C:31]2[NH:30][C:38]3[C:33]([CH:32]=2)=[CH:34][CH:35]=[CH:36][CH:37]=3)=[O:40])=[N:4][N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 118162081H-indole-2-carbonyl ChlorideHCID 677277459-chloro-4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine

Product 1

HCID 67727760N-(3-chloro-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl) [1,2,4]triazol-5-ylmethyl)indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

9-Chloro-4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (0.5 g) was stirred with 2M hydrochloric acid (12.5 ml) at 60° C. for 2.5 hours. The reaction mixture was cooled to room temperature. Sodium hydrogencarbonate was added to make the reaction mixture alkaline. Chloroform and indole-2-carbonyl chloride (0.33 g) were added, and the mixture was stirred for 0.5 hour. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was concentrated under reduced pressure, and the obtained residue was crystallized from ethyl acetate to give 0.2 g of N-(3-chloro-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl) [1,2,4]triazol-5-ylmethyl)indole-2-carboxamide.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customthe obtained residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-8876e720e1d9445e883d22a1242ee547
Source dataset
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05760032

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes