Potassium Hydroxide → 7-Chloro-10-(methylthio)-4H-thieno[3,4-b] [1,5]benzodiazepine

HRID 1605910Notes

Reaction equation

HRID 1605910 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3=[CH:12][S:13][CH:14]=[C:9]3[C:8](=[S:15])[NH:7][C:6]=2[CH:16]=1.[OH-].[K+].S([O-])(O[CH3:23])(=O)=O>O1CCOCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3=[CH:12][S:13][CH:14]=[C:9]3[C:8]([S:15][CH3:23])=[N:7][C:6]=2[CH:16]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 4694097Methyl sulfate(1-)HCID 125216547-Chloro-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-thione

Product 1

HCID 125216627-Chloro-10-(methylthio)-4H-thieno[3,4-b] [1,5]benzodiazepine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a stirred suspension of 0.8 g. of 7-chloro-4,9-dihydro-10H-thieno[3,4-b] [1,5] benzodiazepine-10-thione in 10 ml of dioxane is added dropwise and simultaneously at 30°-40°C., a solution of 0.95 g. of potassium hydroxide in 10 ml. of methanol and 0.8 g. of methyl sulfate. After addition is complete, the reaction mixture is stirred for 3 hours, diluted with methanol and filtered. The filtrate is concentrated to 20 ml., diluted with water and extracted with chloroform. The chloroform solution is concentrated under reduced pressure to give a solid, which is recrystallized from methanol-water to give yellow crystals, m.p. 111°-113°C.

Workup

  1. additionTo a stirred suspension of 0.8 g
  2. additionAfter addition
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated to 20 ml
  5. addition, diluted with water
  6. extractionextracted with chloroform
  7. concentrationThe chloroform solution is concentrated under reduced pressure
  8. customto give a solid, which
  9. customis recrystallized from methanol-water
  10. customto give yellow crystals, m.p. 111°-113°C.

Sources & evidence

ORD record
ord-bf0b1beeed67468691ff6e51069b164b
Source dataset
uspto-grants-1976_04
Patent number
US03951981

Reaction notes

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