Dichloromethane → (E)-3-Chloro-N-(3-chloro-2-propenyl)-N-methylbenzo[b)thiophene-7-methanamine

HRID 1756296Notes

Reaction equation

HRID 1756296 reaction equation
Br[CH2:2][C:3]1[C:8]2[S:9][CH:10]=[C:11]([Cl:12])[C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl.[Cl:14]/[CH:15]=[CH:16]/[CH2:17][NH:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].ClCCl>CS(C)=O>[Cl:12][C:11]1[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][N:18]([CH2:17]/[CH:16]=[CH:15]/[Cl:14])[CH3:19])[C:8]=2[S:9][CH:10]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 147805207-(Bromomethyl)-3-chloro-1-benzothiopheneHCID 19917493trans-1-Methylamino-3-chloro-2-propene hydrochloride

Product 1

HCID 15290083(E)-3-Chloro-N-(3-chloro-2-propenyl)-N-methylbenzo[b)thiophene-7-methanamineYield 74%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2.62 g (10 mmol) of 7-bromomethyl-3-chlorobezo[b]thiophene in 10 ml of dimethyl sulfoxide were added 1.7 g (12 mmol) of (E)-N-(3-chloro-2-propenyl)methylamine hydrochloride and 2.07 g (15 mmol) of ground potassium carbonate. The mixture was stirred for 16 hours at room temperature, and poured into 150 ml of dichloromethane. The organic layer was washed with 100 ml×2 of water and 50 ml of saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (n-heptane). The desired fractions were put together and concentrated under reduced pressure to obtain 2.12 g (yield: 74%) of the above identified compound as an oil.

Workup

  1. washThe organic layer was washed with 100 ml×2 of water and 50 ml of saturated sodium chloride aqueous solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. concentrationconcentrated under reduced pressure
  5. customto obtain 2.12 g (yield: 74%) of the

Sources & evidence

ORD record
ord-160f93a63e6e48c2b3f41ce5f9cd2cec
Source dataset
uspto-grants-1995_08
Patent number
US05440049

Reaction notes

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