Hydrochloric Acid → HCID 20144475, compound

HRID 649014Notes

Reaction equation

HRID 649014 reaction equation
[Br:1][C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][CH3:13])[C:4]=2[S:5][CH:6]=1.C([Li])CCC.[CH3:19][S:20]SC.Cl>CCCCCC.CCOCC>[CH3:19][S:20][C:6]1[S:5][C:4]2[C:7]([CH2:11][NH:12][CH3:13])=[CH:8][CH:9]=[CH:10][C:3]=2[C:2]=1[Br:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12232Dimethyl DisulfideHCID 20144462HCID 20144462, compoundHCID 178418339Butyllithium

Product 1

HCID 20144475HCID 20144475, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To a solution of 2.55 g of N-(3-bromo-7-benzo[b]thienylmethyl)methylamine in abs. ether are added dropwise under inert gas at -70° 13.8 ml (2 equivalents) of a 15% solution of n-butyllithium in n-hexane. 1.9 ml of dimethyldisulfide are then added slowly at -70° and the reaction mixture gradually warmed to room temperature. It is then poured into ice-cooled 2N HCl, shaken and the acid phase separated, made alkaline with NaOH and extracted with ether. The ether phase is dried, concentrated under vacuum and the oil thus obtained directly further reacted.

Workup

  1. additionIt is then poured into ice-
  2. customthe acid phase separated
  3. extractionextracted with ether
  4. dry with materialThe ether phase is dried
  5. concentrationconcentrated under vacuum
  6. customthe oil thus obtained directly further reacted

Sources & evidence

ORD record
ord-44b27b0e3d5e44f882237adc0be22fa3
Source dataset
uspto-grants-1988_04
Patent number
US04737516

Reaction notes

Loading…