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

HRID 1605908
Notes
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Reaction equation

HRID 1605908 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5](=[S:13])[C:4]2=[CH:14][S:15][CH:16]=[C:3]12.O1CCOC[CH2:18]1.[OH-].[K+].S([O-])(OC)(=O)=O>CO>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]([S:13][CH3:18])[C:4]2=[CH:14][S:15][CH:16]=[C:3]12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 4694097Methyl sulfate(1-)HCID 125216534,9-Dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-thione

Product 1

HCID 125216604-Methyl-10-(methylthio)-4H-thieno[3,4-b] [1,5]benzodiazepine

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent
2×

Procedure

To a stirred suspension of 0.7 g. of 4,9-dihydro-4-methyl-10H-thieno[3,4-b] [1,5] benzodiazepin-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 ml. of methyl sulfate. After addition is complete, the mixture is stirred for 3 hours, diluted with methanol and filtered. The filtrate is concentrated to about 20 ml., diluted with water and extracted with chloroform. The chloroform solution is concentrated to give a solid, which is recrystallized from methanol-water to give orgnae crystals, m.p. 113°-115°C.

Workup

  1. additionTo a stirred suspension of 0.7 g
  2. additionAfter addition
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated to about 20 ml
  5. addition, diluted with water
  6. extractionextracted with chloroform
  7. concentrationThe chloroform solution is concentrated
  8. customto give a solid, which
  9. customis recrystallized from methanol-water
  10. customto give orgnae crystals, m.p. 113°-115°C.

Sources & evidence

ORD record
ord-7659c979b1de4cafb4fac39d309ea425
Source dataset
uspto-grants-1976_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03951981

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes