Dichloromethane → (E)-3-Chloro-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methylbenzo[b]thiophene-7-methanamine hydrochloride

HRID 1648626Notes

Reaction equation

HRID 1648626 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.[CH3:14][C:15]([CH3:24])([CH3:23])[C:16]#[C:17]/[CH:18]=[CH:19]/[CH2:20][NH:21][CH3:22].C(=O)([O-])[O-].[K+].[K+].ClCCl>CS(C)=O>[ClH:12].[Cl:12][C:11]1[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][N:21]([CH2:20]/[CH:19]=[CH:18]/[C:17]#[C:16][C:15]([CH3:24])([CH3:23])[CH3:14])[CH3:22])[C:8]=2[S:9][CH:10]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 147805207-(Bromomethyl)-3-chloro-1-benzothiopheneHCID 19917487(E)-N-methyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride

Product 1

HCID 6918069(E)-3-Chloro-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methylbenzo[b]thiophene-7-methanamine hydrochlorideYield 77%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 0.34 g (1.3 mmol) of 7-bromomethyl-3-chiorobenzo[b]thiophene in 3 ml of dimethyl sulfoxide were added 0.246 g (1.31 mmol) of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)methyiamine hydrochloride, and 0.27 g (1.95 mmol) of potassium carbonate under ice cooling. The mixture was stirred for 19 hours at room temperature, poured into 40 ml of dichioromethane, washed with 30 ml ×2 of water, and adjusted to pH 2 with 25 ml of water and 2N hydrochloric acid. The organic layer was separated washed with 20 ml of saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and cooled to crystallize. The crystals were suspended in isopropylalcohol, filtered, washed with isopropyl alcohol and dried to obtain 0.37 g (yield: 77%) of the above identified compound as white crystalline powder.

Workup

  1. washwashed with 30 ml ×2 of water
  2. customThe organic layer was separated
  3. washwashed with 20 ml of saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. temperaturecooled
  7. customto crystallize
  8. filtrationfiltered
  9. washwashed with isopropyl alcohol
  10. customdried
  11. customto obtain 0.37 g (yield: 77%) of the

Sources & evidence

ORD record
ord-38916b635529447ea33d446f863dc0a0
Source dataset
uspto-grants-1995_07
Patent number
US05436354

Reaction notes

Loading…