Ethanol → 5-(2-chlorophenyl)-1,3-dihydro-8-ethoxy-7-fluoro-2H-1,4-benzodiazepin-2-thione

HRID 2112509Notes

Reaction equation

HRID 2112509 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]([F:20])[C:17](F)=[CH:18][C:13]=2[NH:12][C:11](=[S:21])[CH2:10][N:9]=1.[CH2:22]([OH:24])[CH3:23].[H-].[Na+]>C(OCC)(=O)C>[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]([F:20])[C:17]([O:24][CH2:22][CH3:23])=[CH:18][C:13]=2[NH:12][C:11](=[S:21])[CH2:10][N:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 57642320HCID 57642320, compound

Product 1

HCID 576423265-(2-chlorophenyl)-1,3-dihydro-8-ethoxy-7-fluoro-2H-1,4-benzodiazepin-2-thione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.5 g (0.00155 mole) of 5-(2-chlorophenyl)-1,3-dihydro-7,8-difluoro-2H-1,4-benzodiazepin-2-thione (IImm), 10 mL of ethanol and 0.62 g of 60% sodium hydride was heated at reflux for 24 hours. The mixture was cooled, diluted with ethyl acetate and washed successively with water and then brine. The ethyl acetate extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 0.52 g of 5-(2-chlorophenyl)-1,3-dihydro-8-ethoxy-7-fluoro-2H-1,4-benzodiazepin-2-thione (IIg) as a yellow solid. MH+/Z=349.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. temperatureThe mixture was cooled
  4. washwashed successively with water
  5. extractionThe ethyl acetate extract
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-807095ef65c145e5b74a65b2b49f6efc
Source dataset
uspto-grants-2009_04
Patent number
US07524840B2

Reaction notes

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