Ethanol → 2-(methylthio)-4,5,6,7-tetrahydro-1H-1,3-diazepine

HRID 2102292Notes

Reaction equation

HRID 2102292 reaction equation
CI.[NH:3]1[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]1=[S:10].[CH3:11]CO>CC(C)=O>[CH3:11][S:10][C:4]1[NH:3][CH2:9][CH2:8][CH2:7][CH2:6][N:5]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6328Methyl iodideHCID 7365891,3-Diazepane-2-thione

Product 1

HCID 2011542-(methylthio)-4,5,6,7-tetrahydro-1H-1,3-diazepineYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl iodide (0.55 ml, 1.15 mmol) was added to a solution of 1,3-diazepane-2-thione (1.00 g, 7.68 mmol) in acetone (8 ml). The reaction mixture was refluxed for 15 min. EtOH was added to the hot solution to dissolve the solids. After cooling to r.t. hex. was added and the precipitate was collected by filtration, washed with hex. and dried to give 1.79 g (86%) crude title compound which was used directly in the next step.

Workup

  1. temperatureThe reaction mixture was refluxed for 15 min
  2. dissolutionto dissolve the solids
  3. additionwas added
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with hex
  6. customand dried

Sources & evidence

ORD record
ord-36355a4787e74a748322ce6e0bbbafc9
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Reaction notes

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