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

HRID 484529Notes

Reaction equation

HRID 484529 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-3chlorobezo[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. customto obtain 2.12 g (yield: 74%) of the

Sources & evidence

ORD record
ord-f521dfba13654fce870c2495a2571cc4
Source dataset
uspto-grants-1993_07
Patent number
US05231183

Reaction notes

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