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Water → 9-chloro-4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine

HRID 963095
Notes
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Reaction equation

HRID 963095 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[CH:20]=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1.[Cl:23]N1C(=O)CCC1=O.C(OCC)(=O)C.O>CN(C)C=O>[Cl:23][C:20]1[N:12]2[C:13]3[S:17][C:16]([CH2:18][CH3:19])=[CH:15][C:14]=3[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[N:9][CH2:10][C:11]2=[N:22][N:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 124343254-(2-chlorophenyl)-2-ethyl-6H-thieno(3,2-f)(1,2,4)triazolo(4,3-a)(1,4)diazepine

Product 1

HCID 677277459-chloro-4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepineYield 16.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2-Chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (10.0 g) and N-chlorosuccinimide (4.55 g) were dissolved in dimethylformamide (50 ml), and the mixture was stirred at room temperature overnight. Ethyl acetate and water were added thereto. The organic layer was washed with water and dried over magnesium sulfate. The solvent was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give 1.8 g of 9-chloro-4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3d08e756c37c4a6f89b8f915ab07c934
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