Sodium Hydroxide → HCID 18422306, compound

HRID 1281822Notes

Reaction equation

HRID 1281822 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[C:8]3[C:13]4[CH:14]=[CH:15][C:16]([O:18]C)=[CH:17][C:12]=4[S:11][C:9]=3[NH:10][C:4]=2[CH:3]=1.C(S)(S)C.[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>ClCCl.O>[F:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([N:20]3[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]3)[C:8]3[C:13]4[CH:14]=[CH:15][C:16]([OH:18])=[CH:17][C:12]=4[S:11][C:9]=3[NH:10][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 336451,1-EthanedithiolHCID 6451240Aluminum(III) ChlorideHCID 18422187HCID 18422187, compound

Product 1

HCID 18422306HCID 18422306, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

8-Fluoro-3-methoxy-12-(4-methylpiperazin-1-yl)-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine (500 mg) was dissolved in dichloromethane (15 ml) and ethanedithiol (2.10 ml) and aluminium chloride (2.51 g) were added. The mixture was stirred at room temperature for 2 hours. Water (50 ml) was added to the reaction mixture and 10% aqueous sodium hydroxide solution was added until it assumed alkaline. The mixture was extracted with chloroform, washed with water, washed with saturated aqeuous sodium chloride solution and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was separated by silica gel column chromatography (chloroform:methanol=5:1) and recrystallized from ethyl acetate to give 8-fluoro-3-hydroxy-12-(4-methylpiperazin-1-yl)-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine (251 mg).

Workup

  1. additionwas added until it
  2. extractionThe mixture was extracted with chloroform
  3. washwashed with water
  4. washwashed with saturated aqeuous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was separated by silica gel column chromatography (chloroform:methanol=5:1)
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5b7717b63b2c4252a40e86f8b47d2186
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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