Hydrochloric Acid → HCID 86741681, compound

HRID 2119135Notes

Reaction equation

HRID 2119135 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].Br[C:12]1[CH:17]=[CH:16][C:15]([C@H:18]2[N:26]3[C@@H:21]([CH2:22][CH2:23][CH2:24][CH2:25]3)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1.Cl>CN1CCCC1=O.CO>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:12]2[CH:17]=[CH:16][C:15]([C@H:18]3[N:26]4[C@@H:21]([CH2:22][CH2:23][CH2:24][CH2:25]4)[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7815p-ChlorothiophenolHCID 24758Sodium hydrideHCID 13606121HCID 13606121, compound

Product 1

HCID 86741681HCID 86741681, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A solution of 4.1 g (0.028 mole) of 4-chlorothiophenol in 40 mL of dry N-methylpyrrolidinone was added to 0.028 mole of sodium hydride (from 1.36 g of 50% sodium hydride washed free of oil with hexane) under an atmosphere of nitrogen. Then a solution of 5.3 (0.019 mole) of trans-3-(4-bromophenyl)octahydroindolizine in 50 mL of dry N-methylpyrrolidinone and 1.35 g of cuprous oxide was added to the mixture and the reaction mixture was refluxed overnight. Then the reaction was cooled to room temperature, MeOH was added, and the mixture was filtered. The solvent was evaporated in vacuo to a brown oil. The oil was flash chromatographed in SiO2 using 98% hexane, 2% acetone as the eluant. The product was collected in fractions 6 and 7, and evaporation of the solvent in vacuo gave an oil. The oil was treated with ethereal HCl to give a solid salt. The solid was recrystallized from acetonitrile to give 77 g (10% yield) of the title compound as a white solid, mp=198°-201° C.

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. filtrationthe mixture was filtered
  3. customThe solvent was evaporated in vacuo to a brown oil
  4. customchromatographed in SiO2 using 98% hexane
  5. customThe product was collected in fractions 6 and 7, and evaporation of the solvent in vacuo
  6. customgave an oil
  7. customto give a solid salt
  8. customThe solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-053a84ce9e1c4345acae81cc8505210d
Source dataset
uspto-grants-1987_07
Patent number
US04683239

Reaction notes

Loading…