N,N-Diethylaniline → HCID 68856753, compound

HRID 226101Notes

Reaction equation

HRID 226101 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][CH2:12][C:13](Cl)=C)([CH3:4])([CH3:3])[CH3:2].[C:16]1(N(CC)CC)C=CC=CC=1>CCOC(C)=O>[C:1]([C:5]1[C:6]2[S:11][C:12]([CH3:13])=[CH:16][C:7]=2[CH:8]=[CH:9][CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 7061N,N-DiethylanilineHCID 86621043HCID 86621043, compound

Product 1

HCID 68856753HCID 68856753, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-tert-Butyl-2-(2-chloro-allylsulfanyl)-benzene (5.66 g, 23.58 mmol) in PhNEt2 (50 mL) is refluxed overnight. It is cooled to rt, diluted with EtOAc (100 mL), washed with 1.0 M HCl (3×100 mL); dried with Na2SO4; filtered and concentrated. The resulting crude material is purified by chromatography gives the title compound (4.69 g, 23.01 mmol, 98%). 1H NMR (CDCl3): δ 1.54 (s, 9H), 2.59 (d, J=1.3 Hz, 3H), 6.99 (q, J=1.3 Hz, 1H), 7.21-7.29 (m, 2H), 7.53 (dd. J=7.4, 1.3 Hz, 1H) ppm. ES-MS (m/z): calcd for C13H16S (M+1)+: 205.3. found: 205.0.

Workup

  1. washwashed with 1.0 M HCl (3×100 mL)
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting crude material is purified by chromatography

Sources & evidence

ORD record
ord-f735952a52834856acd1665b388a98a4
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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