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

HRID 1648609Notes

Reaction equation

HRID 1648609 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-231ced4b45ca42049b0cab52dfb04004
Source dataset
uspto-grants-1995_07
Patent number
US05436354

Reaction notes

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