Methyl iodide → 2-(Methylthio)-4,5-dihydro-3h-1-benzazepine

HRID 80528Notes

Reaction equation

HRID 80528 reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][C:2]1=[S:12].[OH-].[K+].I[CH3:16]>CC(C)=O>[CH3:16][S:12][C:2]1[CH2:3][CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:1]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 125454261,3,4,5-Tetrahydro-2H-1-benzazepine-2-thione

Product 1

HCID 125454282-(Methylthio)-4,5-dihydro-3h-1-benzazepine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of Example 182B (2.3 g, 12.97 mmol) in acetone (51.9 mL) was heated to 60° C. in and oil bath. Then potassium hydroxide (36.4 g, 649 mmol) was added followed by the dropwise addition of iodomethane (0.811 mL, 12.97 mmol). The resulting yellow slurry was stirred for 5 minutes and then the solids were collected by filtration. The solids were washed with acetone and the filtrate was concentrated to obtain the crude title compound which was used was used without purification for the next reaction.

Workup

  1. filtrationthe solids were collected by filtration
  2. washThe solids were washed with acetone
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2880a2dab2a8448fa0f028bf857775c7
Source dataset
uspto-grants-2014_09
Patent number
US08846663B2

Reaction notes

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