Diethyl Ether → HCID 15581960, compound

HRID 1605675Notes

Reaction equation

HRID 1605675 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].CCOCC.C1([Li])C=CC=CC=1.[CH2:20]([N:23]=[C:24]=[S:25])[CH:21]=[CH2:22]>C1C=CC=CC=1.CCOCC>[CH2:20]([NH:23][C:24](=[S:25])[CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[CH:21]=[CH2:22]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 5971Allyl IsothiocyanateHCID 79752-MethylpyridineHCID 178506676HCID 178506676, compound

Product 1

HCID 15581960HCID 15581960, compound

Reagents, catalysts & solvents 1

HCID 22174802Benzene etherSolvent

Procedure

A solution of 9.3 g. (0.1 mole) of 2-picoline in 50 ml. of anhydrous ether is added dropwise at 15°C. to 50 ml. of a 2.1M solution of phenyl lithium in benzene/ether under nitrogen. The resulting mixture is stirred for 1 hour, then added dropwise to a stirred solution of 9.9 g. (0.1 mole) of allyl isothiocyanate in 200 ml. of anhydrous ether at -50°C. under nitrogen. The mixture is stirred for 15 minutes after the addition is complete and then poured into 150 ml. of dilute hydrochloric acid/ice and stirred. The layers are separated and the aqueous phase is basified with 5% aqueous sodium carbonate solution and then extracted with ethyl acetate. The extracts are dried and concentrated and the residue is recrystallized from benzene/petroleum ether to give N-allyl-2-(2-pyridyl)thioacetamide, m.p. 67°-68°C.

Workup

  1. additionadded dropwise to a stirred solution of 9.9 g
  2. customat -50°C.
  3. stirringThe mixture is stirred for 15 minutes
  4. additionafter the addition
  5. additionpoured into 150 ml
  6. customThe layers are separated
  7. extractionextracted with ethyl acetate
  8. customThe extracts are dried
  9. concentrationconcentrated
  10. customthe residue is recrystallized from benzene/petroleum ether

Sources & evidence

ORD record
ord-6485fb3d3ae7491fbf124c6a470aee9b
Source dataset
uspto-grants-1976_04
Patent number
US03950522

Reaction notes

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